Queen Bees and Other Insignificant Characters
by HelloSunshine89
Summary: Welcome to high society, where only the truly fabulous matter. Don't feel bad if you don't own your own pair of Christian Louboutin sandals and don't have two boys with perfect smiles vying after you. Here you can live vicariously through Rory Gilmore.
1. Take Sweets From Strangers

**Chapter 1**: Take Sweets From Strangers

**Author's Note**: I have to say, it's pretty freaking awesome to no longer be a fan fiction virgin. I enjoyed my cherry popping experience, don't get me wrong (you whores are amazing), but when you write your second story you definitely go into "I'm A Woman, Watch Me Pop Off On You" mode.

So for every one of my crazy fangirls who followed me to this story, welcome. How can I make you comfortable?

I'm glad our ONS meant as much to you as it did to me. I'll try to turn up the heat on our second date.

**Summary/Things You Need to Know/Hitchhiker's Guide to My New Piece**: Come with me as we transport back to a simpler time where Rory was 16/17 and naive. Except I kind of flipped that whole idea on its head, threw Rory into High!Society! and casted a bunch of awesome people to play in my fictional world of the obscenely privileged. I got the idea to throw out Stars Hollow (as the center stage; no worries, I'm putting that frakked up town in here one way or another) from my new love, Gossip Girl. Rory is hopefully going to be an awesome bitch, Jess is well, he's not poor, he goes to Chilton and the story should explain just exactly how I am writing him. Along with Rory at my new!improved!Chilton are the ones who were there (including Tristan) along with Logan, Finn and Colin and then some characters I created on my own accord from other influences.

And Lorelai stayed in society. So yes, slap me with your Prada bag now. I didn't have the pregnant girl rebel. That never happened, at least not in the runaway with the baby way.

If you haven't caught on, the story is in an alternate universe and I think every character, at one point or another, will be OOC.

Hopefully that gives you the background knowledge you need to go into this piece with a certain understanding. Any other questions, just ask. I have a Magic 8 Ball on hand when I write for a reason.

**Disclaimer**: The original morphing idea came from Gossip Girl, as I said above, which means I might steal a few things from that show/book series to create my characters around certain things/relationships. And I don't own the alphabet. I got a letter yesterday saying I had to stop saying I owned all words. Webster totally bums me out hardcore.

* * *

Rory took a sip out of her champagne glass. She glanced around the room, searching for her boyfriend, Logan Huntzberger, who per usual, was nowhere to be found.

He was probably off in some blonde's hair, busy figuring out how far he could shove certain things down her throat.

She hated her mother's parties. But when your mother's profession was "Connecticut Socialite," also known as a glorified party girl, parties with leering fifty-year-old men and gossipy plastic enhanced women was your life.

She noticed Jess Mariano was sitting on the couch with his usual satisfied smirk adorning his lovely features.

He was either stoned or had just gotten a blowjob from the blonde Logan was probably all up in at the moment.

Even though Jess was a pig, Rory had to admit he was Calvin Klein underwear ad gorgeous. And he was her partner in crime when she didn't want to get her stilettos dirty.

Since it looked like her mission to finally lose her virginity had failed, she figured she might as well go talk to Jess.

At least he was entertaining.

* * *

Jess pretended to not notice Rory making her way towards him on the couch.

But really, who could pretend not to notice those legs? They went on forever.

Jess loved when Rory wore those short black dresses. He knew she did it to look like Audrey Hepburn, but he just enjoyed how accessible her thighs were.

And _other_ things.

Not that he'd ever gotten there. Rory was the only virgin left at Chilton (even Paris had swiped her innocence) and Jess knew his chances of getting her to cash in her V-card with him were nearly impossible.

She loved to hate him, which wasn't exactly the most flattering thing. But it could be worse. She thought Tristan DuGrey was an STD infested sloth.

Rory hovered over Jess, giving him her perfect bitch smile.

"So where is your lover boy?" he prodded, knowing exactly where Logan was. Stevie Wonder knew where Logan was.

"Probably off with the same blonde who gave you that satisfied smirk," Rory deadpanned, downing the rest of her champagne.

Jess looked up and smirked. "How about we go into your room, take off our clothes and stare into each others eyes? I'll even listen if you want to cry about him."

Rory chuckled. "How much ass has that line gotten you?"

"I've been up enough Chilton skirts to tell you wool is itchy."

"But only up each one once. No girl goes back to Jess for seconds."

"I just pass them off to Logan when I am done with them."

Rory looked down. "Touché."

Jess faltered. "I'm sorry, I shouldn't have said that. But why do you stay with him when you know right now Miss Blonde is down on her knees in your guest room?"

Rory ignored the fact that Jess Mariano sounded like he cared about how she was feeling and kept her walls securely up. "Trust funds are very attractive."

"We all have trust funds."

"Ah yes, but none like Logan's."

"And people think you're nice."

"We all have to climb the social ladder someway."

Jess smiled. "I have a proposition for you."

"I'm not letting you seduce me."

"I'm not trying. I know how much you love being a bitch."

"It's what I live for."

"So why not make Logan jealous and get rid of that pesky virgin label all at once?"

Rory laughed. "I'd rather let Cujo deflower me."

"I love it when you talk dirty."

Rory rolled her eyes. "And it's not like I'd enjoy it. No one enjoys their first time."

"True. But I'm Jess Mariano. I'd make sure you enjoyed your first time."

"How thoughtful of you."

"If you please me, I'll please you."

"Try again after I've had more than one glass of champagne."

Jess shook his head. "You're such a tease."

* * *

Logan entered the party, readjusting his tie and running a hand through his hair, immediately spotting his girlfriend having an actual conversation with Jess Mariano.

The guy was his best friend but he knew for a fact Rory hated him.

She must be desperate for entertainment.

Logan walked up to her, placed an arm protectively around her waist and kissed her cheek.

"Hey Ace," he whispered in her ear.

Forcing a smile like the good Gilmore girl she was, Rory gave him a brief flash of her perfect teeth and turned her attention back to Jess.

She might not be willing to cash in her v-card to Jess, but what harm could a little flirting do?

"Why are you talking to Jess? You loathe Jess."

"Aw Rory, is that true? You find me loathsome?"

"Not entirely."

"Did you hear that Logan? Your girlfriend is warming up to me."

"Shocking."

"It shouldn't be. I know how to warm girls up. I'm a pro at finding those pressure points."

Rory forced herself to blush.

She noticed that Jess' tie had come loose and thought fixing it might make Logan's blood boil.

For all his fault's, he was insanely possessive of Rory.

Okay, maybe that was a fault as well, but Rory found it utterly irresistible.

She bent down, starting her giggle a bit early and grabbed a hold of Jess' tie. "Just thought I'd tighten it back up," she said, with a grin.

She didn't mean for it to happen, but her nose grazed with Jess' for a brief moment.

She stared at him. A smirk wasn't adorning his Calvin Klein features at Rory's attempt to make Logan jealous.

His eyes were locked on hers.

No, she thought to herself, there was not tension in that nose graze.

Snap out of it, Rory Gilmore. You cannot have any type of feelings except hate for Jess Mariano. He was a womanizer. A dog. Not her knight in shining armor.

Jess just sat there. A nose graze and he was hard.

What the hell was going on? Jess Mariano did not get hard from a nose graze from his best friend's bitch of a girlfriend.

But she did still have a hold of his tie.

Why wasn't she letting go?

Logan cleared his throat, breaking up their moment of confused tension.

He grabbed Rory's hand, pulling her away from Jess.

* * *

Logan jerked her into a corner so everyone wouldn't witness their little 'spat,' as Emily called them. Everyone seemed to have, at one time or another, witnessed a Rory/Logan 'spat.'

But the nose graze had already done its damage. The party was a flutter with the news that Rory was cheating on Logan with Jess.

In an hour, she'd be pregnant with twins, one belonging to Logan, the other Jess'.

It didn't matter that it was public knowledge that she was still as pure as snow, the true Virgin Mary of Chilton.

Oh the power of gossip.

Logan had a hold of one of her wrist, but she quickly squirmed her way out of his clutches.

"Rory, what was that?"

She acted like nothing had happened. "What was what?" She asked, grabbing another glass of champagne from a passing waiter and downing it in one sip.

She wiped her mouth with the back of her hand.

Logan fumed. "You know what I'm talking about," he gestured toward Jess, who was busy chatting up Rory's mother. "That little show you put on with Jess."

"That wasn't a show. I was fixing his tie."

"Your noses touched."

Rory choked back the vomit that was forcing its way up her throat. She wanted badly to hurl all over his Armani suit.

Instead, she gave him a sinister smile. "There was no nose touching."

"You were practically nose humping."

"Nose humping, Logan? Seriously?"

"Don't say my name like I'm a child."

"I hate Jess. I would never 'nose hump' with him, whatever that means." She fished around in the pockets of her Marc Jacobs dress for a cigarette.

"I know you hate Jess, but I also know how much you love your little games."

"There are no games. I fixed his tie. I didn't take him to the pool house and blow him until he was walking around going on and on about nose humping." Rory gave him a cold smile. "Oh wait, that's you."

Logan shifted, visibly uncomfortable with the direction this conversation had taken. He didn't say a word.

Rory shook her head. "You don't even try to deny it anymore." Her eyes had taken on a glassy shine. "Damn Logan."

"Rory…" Logan started, in a warning tone.

And then, she lost it. "Rory what? What, Logan? This is my mother's party, at my house, which means I can speak to you however I want." Logan reached out for her hand, but she pulled back.

"No, don't touch me! Get away from me!" She stopped her tirade, realizing all eyes were on her.

She looked around, then down at her feet, her cheeks turning a deep shade of pink.

Mumbling an "excuse me," she stalked off to her bedroom, slamming the door.

Logan looked up and locked eyes with Jess, whose features held a satisfied smirk for a moment before he glanced back down into his glass of scotch.

* * *

Cue the gossip Hartford hounds to put their spin on this moment.

"I hear Lorelai is sending her off to rehab for her drinking problem. Did you see how she downed that glass of champagne? She is a seriously troubled young woman."

Tristan's mother sure was desperate to make someone else's child out to be an utter embarrassment.

"I thought she was going to rehab for her sex addiction?"

Never count on your friends to defend you. That's one lesson you learn in society; even the bitches that suck up to you in the courtyard, commenting on how much they covet your Coach purse, will enjoy your mini breakdowns.

"Wait, isn't she a virgin?" asked the one sensible girl in the group, which meant she was probably just a freshman.

Freshman only served one purpose and that was to service the upper class boys.

"Not since she started getting it on in the pool house with Jess." Because of course, Rory would go_ there_.

"The pool house? That's so trailer trash," says the girl whose mother climbed the social ladder by sleeping with any businessman with a bad heart. Too bad she started out in a trailer park in Riverside. That's just socially unacceptable.

"I just hope the poor girl gets the help she needs. We don't need another Girl Interrupted on our hands." Ah yes, be the sensible mother, Mrs. DuGrey. If you're going to spread gossip, at least be a peach about it and hope the "poor child" is saved.

"Maybe she's just following in E's footsteps." Who is E? Oh, you mean _that _E. If that's true, this will be a a fun year.

"I heard E got kicked out of boarding school and is headed back here." That's actually believable. E was only good at two things and both have one word in common: blow.

"R is going to have a fit. Everyone knows E and L got it on right before she went to boarding school. R's mom walked in on them doing it on R's bed." That's classy. I hope Lorelai at least bought her new sheets.

"No way!" These freshman really need a 101 class on the rules of spreading gossip. Never question; just make it even more unbelievable, so unreal that it becomes real.

"Way. And I heard E got pregnant, had the baby and sold it for cocaine money." Let's hope she got a good deal.

"I don't think so. I heard she was a model in France." Model or crack baby? Which do _you_ believe? Remember, this is high society.

"When you're that thin, you never show." You might want to put down that doughnut, sweet cheeks.

"She probably didn't even know she was pregnant. She probably went to the bathroom and boom, out fell a baby."

* * *

Jess couldn't help but smile at what he was overhearing. The best and worst thing about the life of the insanely privileged was how ridiculous the gossip was.

If E really was returning, the wrath Rory released on Logan was just a preview of what she was going to do to E.

He imagined total life destruction would be her plan of action at the news of her ex best friend's return.

He thought for a moment about going to check on Rory but quickly realized checking on her would make it appear that he cared about her.

CARED.

Jess Mariano did not care about girls, especially a girl like Rory Gilmore.

What was going on with him? Was he experiencing feelings for someone other than himself?

He shook off his lapse in judgment as a side effect from the weed he smoked right before this party.

The only way to get through social engagements was to a) get wasted off of champagne at the party.

But that option could lead to you humping the wrong person or having a Rorylike meltdown, so there was also b) smoking a joint prior to arriving.

Your eyes were dilated, but the truly fabulous can get away with sunglasses indoors.

And then there was c) having sex in a guest room while the hors d'ouvers were being served and your parents yammered on about how it would be tough for you to choose between Yale, Harvard and Brown (the college version of The Hamptons for the wealthy).

Jess preferred options b or c, but lately, he hadn't partaken in option c as much

But don't tell anyone at the party. He had a reputation to keep intact.

* * *

Rory had her face buried in one of her ultra soft goose feather pillows, snot staining the perfect white sham it was encased in and mascara dripping off her cheeks.

She heard the distinct 'knock, knock' sound at her door and knew it was her mother.

"Enter if you must," she bellowed, in her most dramatic voice.

"Are you auditioning for a remake of Godfather III or something?"

Rory jerked her head up from her pillow, giving her mother the perfect WTF look, furrowed brow and all. "What?"

"You're little performance out there was more dramatic than the original Sophia dying scene." Lorelai clutched her stomach, mocking the scene. "Daddy," she whispered and fell over.

Rory, even though she didn't want to, cracked a smile.

Lorelai stayed on the floor. She liked to lay on the floor because, as she said, 'The carpet cost more than she ever would, so she might as well cuddle with it as much as possible.'

"And the way you said 'enter if you must' was more dramatic than anything Lauren Conrad will ever do."

"I'm the east coast version of Marissa Cooper."

"Please don't start throwing chairs in the pool."

"I'm not sure if I'll be able to control my rage."

"Does mommy need to send you off to rehab?"

Rory laughed. "Is that what they are saying out there?"

"I just found out you have a sex addiction. Rory, is there something you need to get off your chest?"

"Obviously boys."

"Well I guess sex addiction could encompass porn. Are you addicted to porn?"

"'One Night in Paris' really didn't do anything for me."

"It was more of a suspense movie than a sex tape."

"I still wonder about who called her."

"But you never think about the sex."

"So really, it was a Hitchcockian snuff film."

"If it had a bald midget that randomly appeared in Paris Hilton's vagina, it would have been vintage Hitchcock."

Rory swallowed a lump that had suddenly formed in her throat. Was she about to cry over Hitchcock being placed in Paris Hilton's vagina?

Well, no.

That wasn't why the she was unable to swallow an invisible lump.

She sighed. "I'd rather not talk about vaginas."

"I'm not talking about penises with you."

"Did I say I wanted to talk about penises?"

"Okay, I'll cross off all genitalia talk from this conversation." Lorelai eased her way into the reason she had found her daughter with mascara stained cheeks. "So, how's Logan?"

Rory rolled her eyes. "I thought we weren't going to talk about genitalia."

"What did Logan do to deserve dick status today?"

"I'd rather not talk about it," she mumbled, searching her pockets again for that cigarette she still hadn't found.

"Well, how's Jess Mariano?"

Rory stopped. Her eyes quickly shot up and locked with her mothers. "Why would you ask about Jess Mariano?"

"I saw you two chatting prior to your fight with our favorite male genitalia and just wondered if they were in anyway connected."

"When did you become Nancy Drew?" Rory barked, defensively.

"So something did happen with Jess," Lorelai responded in her motherly 'I know so give up on the charade' tone.

"Nothing happened with Jess. I fixed his tie to piss off Logan and it worked."

"Shouldn't you be doing cartwheels on top of the table instead of hiding from society since your plan worked?"

"Cartwheels would make the soufflés fall."

"So you cried to protect the soufflés?"

"It was just a fight, mom."

Lorelai sighed. She wasn't a fan of Logan's. The trust fund didn't make up for his dog like tendencies. And he didn't win any points with her when she found him trading croissants for cocaine at their last society brunch.

But let's be honest, isn't a cocaine brunch tastier than a plain ole croissant?

"Well your grandmother spun it quite nicely."

"That's because she knows every other woman out there is pawing at Logan for their daughter."

"Or for herself."

"This town isn't short on MILF's."

A silence hit the room hard, Lorelai giving her daughter a chance to talk about whatever had happened while she was adjusting Jess Mariano's tie.

Rory's life was one very long, very tedious movie; the movie that no one checked out from Blockbuster except for the lonely girls who never went out on Friday nights.

She was Audrey Hepburn in an extended version of _Breakfast at Tiffany's_ meets _Lord of The Rings_. It was full of diamonds, but painfully long.

But Rory didn't make a peep, instead opting to write this part of the script with an inner monologue.

Oh how tragic her life was. Hamlet had nothing on Miss Rory Gilmore.

Lorelai stood up, trying to smooth out the wrinkles that had appeared in the five minutes she'd been lying on the ground.

The rich didn't wear wrinkle proof materials.

She started to leave. "I better go back out there…" she began, but Rory quickly cut her off.

"What is your take on a nose graze?"

"Huh?"

"You know, you lean forward, he leans forward and boom, a nose hump happens."

"A nose hump? I don't think noses can hump."

"Whatever. But your noses graze and you linger."

"Linger how so? Like did you linger because you humped his nose so hard it started gushing blood or was it a _linger_ linger?"

"What's a _linger_ linger?"

"You were about to kiss him, weren't you?"

"Kiss who?"

Rory started scratching her neck. When she was nervous, she developed a rash on her neck.

Lorelai rolled her eyes, opting to play dumb. "Whomever you experienced this powerful nose graze with."

"I never said it was powerful."

"You lingered."

"Just for a moment!"

"You called it a nose hump. Humping is a pretty powerful word. People replace certain other words with humping."

"There wasn't nose sex!"

Lorelai took a step back, almost stumbling in her shock. "Do you like him?"

"Like who?"

"Your partner in nose humping!"

"Nose fornication isn't even real. It's something Eskimos do. I must have been drunk off champagne and my reflexes were slow."

"It's okay to want to kiss someone who's not your boyfriend."

"What kind of advice is that? You're my mother. You aren't supposed to advise me to cheat."

"Did you want to cheat?"

"Not with him. He's insufferable."

"Rory, you're getting that rash on your neck."

"I know! Nose fornication has given me a rash!"

"If he is affecting you like this…"

"No. I will always love Logan. Logan is the reason I have this rash. Logan and his need to devirginize every girl but me, his girlfriend! His perfect girlfriend!"

But didn't she just say…

Lorelai shifted uncomfortably. "Rory, I think you've forgotten I'm your mother and we agreed to pretend you are a virgin until you are on social security."

"You can't expect me to never have sex," she mumbled.

Lorelai paused. She thought of a way to reason with her daughter about Jess. "It wouldn't be the worst thing in the world if you had a Mr. Darcy."

"I already have a Cary Grant."

"Who you knew when he ate glue. Maybe you shouldn't be planning your future with a boy who once ate glue."

"And you want me to go off and nose hump with a boy whose one goal in life is to get up every Chilton skirt before he graduates?"

"It's a noble adventure."

"Mother!"

"This will be the last thing I say…"

Rory rolled her eyes. Her mother would always have the last word even if it was 'I win, you lose, naa naa boo boo.'

"…I'm not saying go off and nose hump with the boy who shall remain nameless. I know his reputation. This town's Miracle-Gro is gossip. But there's something there."

"A shared hatred for each other."

"Well then maybe you can bond over being the president of each other's haters club."

"Because that is how all great romances begin."

"Maybe you need to brush up on your Austen."

Rory folded her arms over her chest, puffing up like a blowfish, her blood pressure rising each moment she wasted talking about Jess.

But didn't she instigate the conversation?

"Your last thing to say clock has officially run out."

"I need to go check on the food anyways. The shrimp cocktail is about to become toxic and I think my waiters relieved themselves in the pumpkin soup, so I have no confidence that they won't serve the deadly shrimp."

The urge to vomit hit Rory again. "I ate the pumpkin soup."

Lorelai smiled. "Well at least urine is sterile. And I heard they did worse to the crème brulee at the Anderson's last week."

Rory covered her mouth with her hand realizing what worse was. A thousand little sperm had been swimming around in everyone's stomach in Hartford for the past week.

Ew.

* * *

Lorelai would take a little piss in the pumpkin soup over sperm on the dessert tray any day.

It was well known that the boys in the penguin suits didn't exactly relish serving the likes of Jess Mariano who was known to take the female wait staff to the bathroom and find interesting ways to use up all the shampoo.

He owed Rory over a hundred dollars in Fekkai apple cider clarifying shampoo.

At least he was clean in _one _way.

And the wait staff feared her Hulk of a mother, so the only way to retaliate was to put bodily fluids in her lobster crème sauce.

Lorelai exited Rory's room, pulling the door shut with extra care so the gossip wouldn't start up that Rory was having an Emily Rose type fit and she was rushing off to find a priest, a clergyman or some type of sedative.

Although, there was no short supply of Valium in high society, so if she needed one, the hands would fly in the air like someone had started the wave.

Her senses were suddenly attacked by the faint smell of Chanel No. 5 and French cigarettes.

"How is she doing?"

Lorelai pounced back, startled that her mother, in Lorelai's mind, had appeared like the bunny in a magic trick.

"God mother, how do you do that?"

Emily sucked on her bottom lip, then violently clicked her tongue. "What? Stand upright? It is this magnificent thing called evolution."

"Damn those apes for achieving higher thought."

"Would you propose we'd be better off if we all still walked around on all fours?"

"Some of us already do."

"I do hope you aren't referring to that ludicrous sexual position."

Lorelai smiled, coyly. "No, I am of course referring to people like Grizzly Man."

"Grizzly Man? What is that, some farfetched superhero?"

"It was a TV show about this man who thought he was a bear trapped in a man's body. He was mauled in the final episode."

"We don't mourn stupidity in this family, Lorelai. It's why we didn't attend your great-aunt Gabel's funeral."

"I thought we didn't attend her funeral because they lost her body."

"She was also a drunk who kicked puppies, so either way, we wouldn't have attended the funeral." Emily sighed. "Anyways, how is Rory doing?"

"I have to break the news to her that if she kicks puppies and likes her scotch, no one will attend her funeral, so I don't know how she is going to take that blow."

"Seriously Lorelai, I saw her little squabble with Logan."

"She didn't want to talk about Logan."

"You force her to talk about it. That is your motherly right."

"I believe she banished all genitalia from the conversation, which included Logan."

"Then what did you two talk about?"

"An exit strategy for Iraq."

"That involved Jess Mariano?"

"Were you snooping on us?"

Emily looked down into her now empty champagne glass. "I…"

"You didn't steal a piece of my crystal and hold it up to the door, did you? You know how I can't have smudges on my crystal. It was Aunt Susan's."

"Elvira's. Anyways, I just have remarkably good hearing."

"My mother, the dolphin."

Emily's face transformed into a shade of pink that matched her well thought out suit. "Why were you two discussing that boy? He is nearly pornographic."

"He's no Ron Jeremy."

"Pardon my language, but he fucks anything with two legs."

"Mother!" Lorelai squealed with delight.

"You know it's true."

"I'd hope not because dad has two legs."

"You know what I mean. You can't let that boy bother Rory."

"I think Rory can handle Jess without our guidance."

"But she has Logan…" Emily whined.

"Who is definitely pornographic."

"Mitchum pressures the boy. It's expected that he would rebel."

"And you think James doesn't pressure Jess?"

Emily started to become frustrated with Lorelai. "Rory and Logan are Hartford's Charles and Diana."

"And now Charles is with Camilla."

"But Diana and him remained quite close before she died."

"They shared children. Rory and Logan do not share children."

"One day they will. Perfect blonde haired, blue eyed children."

"I didn't know red heads pimped the Aryan race. Go Hitler, whose philosophy is obviously still alive in 2008."

"If she had children with Jess, they'd probably inherit his awful brown eyes."

"She's not having children with Jess. She doesn't like Jess!"

Emily smiled. "That's all I needed to know. As you were."

"As I were what? I'm not a statue."

* * *

Rory still had her head shoved under her pillow, nearly suffocating herself she was pressing down so hard, when she heard the distinctive happy tone of her cell phone.

At first, she didn't move, attempting to ignore what was most likely a drunken text message from Logan; but her curiosity took over her hands and she reached into her pocket, taking out her phone.

The text message was from a number she didn't recognize, but she hit the 'read' button anyways and read something that was more terrifying than Godzilla, her mother without makeup and the thought of sex with Jess Mariano.

"E's back."

Rory couldn't stop the urge to vomit this time.

Her black kitten heels were definitely ruined.

But at least that pumpkin soup was gone.

_Thank god E's back. Rory's life had become way too simple without her._

* * *

**Ending author's note**: I left E's name E for the time being because I am mulling over different E names. Let the mystery eat you up inside. What if her name is Enemy? That'd make it pretty obvious who the bad guy in this story was. Wouldn't that be totally boss if people were named Hero and Villain and stuff like that? Maybe I'll name my kid Frenemy. That's a winner.

As you could probably tell, I set up the possible love triangle right away. Right now it's more of a triangle of confusion/hate/lust but I'm sure it'll produce something awesome. That or a new strand of syphilis.

Working in the gossip/gossip girlishness comments on the gossip is utterly fantastic. I hope you enjoy the little window into my high society through my version of the Chilton Gossip Girl.

**Reviewers**: Remember that I am mentally unstable so every time you are mean to me, I die a little inside.

I kid! I'm totally medicated, so my moods are somewhat stable.

Let's cut to the chase here. Will you stay in this house and continue to rock my world?


	2. Between Love, Hate and Rory's Knees

**Chapter 2**: Between Love, Hate and Rory's Knees

**Author's Note**: Maybe my goal will be to have my story and chapter titles get more and more inappropriate as the story goes on. Or I'll just take a golf club and whack you over the head with all the sexual innuendo and whatnot. This title is pretty PG (I've seen Hannah Montana episodes that are more provocative). But, if I start using parts of anatomy in my titles maybe that'll really be pushing it.

To all those I didn't respond to because you don't have an FF account or you don't think I'm important enough to read the response I sent you, much thanks for loving me almost as much as I love you. Seriously, the response I got to this story was a bit unexpected, but totally awesome. Hopefully I won't blow. It. (see, right there I was going for the sexual innuendo thing again. Man I'm messed up).

**Disclaimer**: Don't try to be this awesome at home kids. It's for professionals only. But even though I say this, think about all those kids who tried the Jackass stunts at home. So really I should just type blah, blah blah...

Same effect, right?

* * *

She knew she couldn't avoid that shock of blonde hair for the rest of her life.

She'd actually had many dreams about what she would do when she saw E again.

What they'd say. What they'd drink. How long it would take for her to strangle her to death.

It'd probably start with a hello (it was a standard greeting that even those in high society tended to use).

She'd only have time for one drink. And as soon as E brought up Logan, Rory's hands would strangle every single bubble gum breath out of her.

It's not that she hated E; she just thought she was better off dead.

Or in a nunnery.

But E coming back now just didn't fit into Rory's social calendar. She could have penciled her in sometime next February, but right now, she had better things to do.

Lose her virginity.

Kill Jess Mariano.

All were things she needed to do before E returned to shove her blonde hair in her face.

She stared at the blank word document in front of her, the blinking cursor mocking her inability to put any coherent thoughts onto the page.

It should be easy to create any entire document of ideas on how to destroy someone's life. Rory was the master, commander and fucking queen of hearts at turning bright futures into trailer park heiresses.

In case you are unfamiliar with the term trailer park heiress (a seeming oxymoron), don't feel left out. It was a phrase created by Rory Gilmore's buzzing heard of bees.

She'd spayed Tristan DuGrey, nurtured Paris Gellar and driven countless other girls insane.

But when it came to E, she knew her normal five-step life destruction plan wouldn't cut it. E used to be her best friend forever (carve that into a tree!). E wouldn't flinch if Rory posted pictures of her walking out of the free clinic. She'd laugh and say the free condoms really weren't something a girl could pass up.

The next day every freshman, who the day before was licking Rory's yogurt spoon, would be caught at the free clinic, everyone's favorite new hot spot.

No, with E, Rory needed a machine gun leg, metaphorically speaking.

_Wait, what? Did anyone see machine gun leg as fall's new trend in Vogue?_

Miss 2300 on her SAT practice test was going to have to get her Manolo Blahnik over the knee suede boots a bit scuffed up to make E disappear, yet again.

Thank god they were from 2006, nearly vintage.

Rory noticed the little messenger icon was dancing on her dashboard.

She saw that Jess Mariano had sent her an instant message.

Cue the over-the-top groan.

_Jess:_

_Read E was back. Just making sure you hadn't offed yourself yet._

She rolled her eyes at his attempt to flirt with her over instant messaging.

Why had she not blocked him again?

_Rory:_

_I'd only off myself if a camera crew was present._

He replied back, instantly. Rory had a flash of some girl on her knees in his bedroom.

She shook that thought of her mind simply because she'd vomited enough for one night.

And she'd taken a vow to pretend genitalia no longer existed.

Obviously, someone had not read "Our Bodies, Ourselves."

_Jess:_

_Attention whores are my favorite kind of whore._

_Rory:_

_I thought any whore worked for you. _

_Jess: _

_I have certain whore requirements. _

_Rory: _

_I don't think there is training to be a whore. If you need training, you've obviously landed yourself in the wrong profession._

_Jess: _

_I don't think Chilton's last virgin can give advice on how to make it as a whore. _

Rory blushed. The virgin word always led to hot pink creeping its way up her neck.

She smiled at what she was going to type next.

_Rory:_

_So how is Louise doing? Does it upset her that you're talking to me while she's getting carpet burn?_

The cursor sat still, Jess taking longer than before to reply.

Then in came his response. She was sure a smirk was attached.

_Jess:_

_She knows she alone can't do much for me. _

If Rory wasn't blushing before, her whole body was now radiating heat. She needed a bath. Or to think about _other _things.

_Rory:_

_You're so disgusting. I'm not partaking in aim sex with you. I'm signing off right now._

Before she could sign off, Jess sent her a final reply.

_Jess:_

_Don't forget to go to confession tomorrow to wash away all those thoughts I know you're having right now._

_Rory:_

_Don't forget to get tested, asshole. _

She was too riled up to fall asleep at this moment; even her Chinese sleep chants and an aromatherapy bath couldn't calm her down.

She needed pie. She needed to gorge on an entire pie.

Or maybe what our perfect little virgin needed was to taste the forbidden fruit.

Maybe she needed to get laid.

We don't want our Queen Bee to suffer the effects of replacing food for sex. We all know what happened to Kirstie Alley.

Jenny Craig was not an acceptable career outlet for a Gilmore.

* * *

Rory entered the kitchen and saw her mother shoveling spoonful after spoonful of chocolate crème pie into her mouth.

Emily must have struck.

She lifted a spoon, silently inviting Rory to join her in a pity fest over pie.

Rory sauntered over to the kitchen table, accepting the spoon and the invitation to take part in 'whose life sucks more' part deux.

"Emily said I was fat," Lorelai sighed, taking another bite of pie.

"E's back."

Lorela's spoon slowly tumbled to the floor, as did her jaw. "I thought she was sent away to boarding school?"

"She was," Rory responded, in a bored tone.

"And now she's back in Hartford? Why?"

"To ruin my life."

"E never did play nice."

"You know what she'll do first to celebrate her homecoming?"

"Logan?"

"Logan is over her."

"I'm sorry. I don't trust him. He's way too in love with his penis."

"He'd get Chlamydia."

"Then you better get him disinfected the next time you see him."

Rory's eyes turned almost black. "I have to get rid of her. I can't let her come back to Chilton and pretend nothing happened."

"You can't kill her." Let's _hope_ there won't be any dialing **M** for murder in this saga.

"I could hire someone to kill her."

"I think the pie is going to your head."

"Do you have a better idea on how to get rid of her?"

"Something legal would be nice."

"Veronica never got caught in _The Heathers_."

"I'm going to pretend you didn't say that."

"I'd just need to find a Jason to help me get away with it."

"Maybe you need counseling. Maybe all this talk of murder is your repressed feelings about your father leaving when you were five."

"Oh, who cares about dad? He sends money and Manolo's."

"Are you projecting your anger at Logan on E?"

"Why do you care about E's well being?"

"I care about the Hartford police not dragging my seventeen year old daughter off in cuffs and pearls. You know Michael Kors won't visit you in prison."

Rory shoved another spoonful of pie into her mouth, leaving the spoon in there long enough to lick every single calorie off. "I wouldn't leave fingerprints."

Lorelai covered her ears. "If I can't hear what you are saying I won't have to testify against you."

"Unless you leave fingerprints or semen the cops never find you."

"Well, it's a good thing you don't have the option to ejaculate all over the body."

Rory sighed, adjusting the straps on her nightgown that were digging into her shoulders. "I can't think of a rumor to spread that isn't true. Everything I could say, she's done."

"You could say she's a female hyena."

"Huh?'

"They have mock penises."

"She spreads her legs too often for that lie to work."

Sometimes Lorelai was astonished at the words that came out of her daughter's mouth. "I can't believe I raised such a mean girl."

"I'm the queen bee at Chilton for a reason. You don't get to where I am by simply smiling and looking like Snow White."

"Then use your little army of bees to brainstorm on how to get rid of E."

Rory rolled her eyes. "They're lucky to have a firm grasp on the English language."

"What about Paris? I think she knows at least five languages."

"I do respect her."

"She's your only rival at Chilton."

"She put up a good fight."

"And I'm sure she has no use for E."

Rory flashed her mother a wicked smile that appeared even more evil in the dark. "Maybe I won't have to resort to murder."

"That makes mommy very happy. You just wouldn't look good in orange."

"My skin tone does not agree with that repulsive color."

Lorelai yawned, then stood up, heading off to her bed that was too large for one person. It had to make her feel extremely lonely every time she was reminded only one side of the bed was ever used. "I'm off to bed."

"I need to go plot."

"You're such a little evil genius."

"It's the bit of grandma that wore off on me."

"You never did play well with others."

"I just don't like to share."

Irony.

That statement was drenched with Dolce Vita perfume in irony.

For a girl who didn't like to share, she didn't seem to flinch at how many girls knew whether Logan preferred boxers or briefs.

But in her mind, she wasn't sharing Logan, because sex was irrelevant. In the end, she was the girl he'd marry.

No one else would look as stunning in a Vera Wang dress.

Emily had Mindy Weiss on speed dial in preparation for the day Logan dropped to his knee for something that required pants.

But was seventeen-year-old love really that predictable? And wasn't there a certain boy who would love nothing more than to see what was under her stockings?

You might know him; he was the guy who was not going to go away, no matter how hard Rory pushed.

He was not one to be discouraged if you didn't let him in the front door. He was quite the fan of entering through windows.

And exiting when the father or boyfriend (or husband) returned home.

Jess Mariano was made to be the other guy.

He couldn't help that he knew how to please the female species.

And right now, his best friend wasn't pleasing the most perfect of the female species at Chilton.

E returning and a love triangle? Could this year get more perfect?

Only if someone was shoved in a pool because R caught L with E and a catfight ensued.

Of course, the standard threesome would suffice as well.

* * *

Rory gripped her coffee cup, anger pulsing through her veins.

There she was. That blond haired coke head was standing in Headmaster Charleston's office, flashing anyone who passed a cotton candy glossed smile and giving every prepubescent freshman boy a little 'I Might Want You When You Can Get It Up' wave.

She hated her.

She wanted to run into Charleston's office, politely smile at Miss Higgins, the criminally unfashionable assistant, and toss her coffee on E.

A few coffee burns would just be a warm up for what was to come. And really, what damage could a 140 degree latte do?

The always-anal Miss Gilmore requested her lattes be at the perfect temperature of 140 degrees. 150 would not do; 130 and she'd make the poor underfed barista cry.

It had to be 140.

If Rory cared that much about the temperature of her latte, what was she going to do to E?

Paris Gellar, in her dreadful knee high grey stockings, walked up to Rory, nervously adjusting her headband.

Ever since the day Rory dethroned Paris Gellar headbands had made her uncomfortable.

They were one of Rory's signature pieces.

She always feared Rory would ban her from wearing them. Not that she'd listen.

Rory might have won the war, but Paris wasn't about to raise her white flag. She certainly wasn't a subscriber to Gandhi's philosophy.

One day, she'd earn her nickname Bonaparte back.

"So is it true?"

Rory sighed, already bored with Paris' question. "What?"

"Everyone is saying you're being shipped off to rehab."

"For what?"

"I believe Franci diagnosed you as a depressive alcoholic sex addict."

"I do love Franci's Freudian tendencies."

"I don't believe the sex addict part."

"It's hard to be addicted to something you've never partaken in."

"And the alcohol part?"

"I didn't expect you to fall into the gossip world, Gellar."

"If Robert Downey Jr. can get caught with blow wandering into strangers homes, so can the great Rory Gilmore."

"I like the sound of that."

"The blow part?"

"The great in front of my name."

Paris rolled her eyes. "You love this, don't you?"

"If they're not talking about you, you really don't matter."

"So how's E?"

"Probably infected."

"Already? I figured it would take her at least a day before she found her way back into the maintenance closet with Jess."

"She had to find someway to distract herself on the plane ride back, I'm sure."

"If Jess is missing during first period, we'll all know where he is."

"You can normally find me in the 2nd stall in the girl's bathroom if either of you want to stop by," Jess stated, standing dangerously close to Rory's body.

Paris groaned at the presence of Jess Mariano. "You really don't know when you're not welcome, do you?"

"Rory and I are best buddies now, aren't we?" he smiled at Rory, daring her to deny it. Daring her to deny the nose hump, the instant message; to pretend the sheer tension between them in this moment didn't exist.

He was double dog daring her with his eyes.

"Rory, do tell me Jess has fallen and bumped his head?"

For a moment, Jess' elbow grazed against Rory's arm. It was too quick for Paris to notice, too quick to even look like it was done on purpose.

But Rory felt it. She knew what game Jess was playing. She had played this very game often when Logan was around.

"I wouldn't define our relationship as best buddies."

"Relationship?" Paris asked, with her eyebrows.

"I don't mean relationship. I mean…" she trailed off, unsure of what she meant.

"What do you mean?" he asked, curious as to what she was getting at.

Or more curious as to what words she was consciously admitting.

"Jess, go off and hump something," Paris suggested, uncomfortable with what was going down between Rory and Jess.

"Not before Rory answers my question."

"I'm not answering your question."

He smiled. Without answering his question, she'd answered his question. "I like your stockings. It's nice to see your knees."

"Don't look at my knees."

"Why not? You have nice knees."

"Are you going to write a poem about her knees?" Paris was amused at his attempt to flirt with Rory.

Rory bit her lip, unable to control the smile that was plastered on her face. She looked ridiculous, smiling at Jess' inability to keep his eyes off her.

Before the party it would have disgusted her; before the nose graze she would have made some bitchy comment and stalked off, leaving him only her ass to long after.

But today she stood there, waiting for him to say something else inappropriate.

"I'd rather write a poem about taking off her stockings."

"Remind me to wear tights from now on, Gellar."

Jess smiled. This was too easy. "Why, are you cold? I'm sure I could find a way to warm you up."

"Really? And how would you do that?" Rory asked. Paris gawked at her. What was she doing? Was she flirting with him? HIM?

"You can follow me into the bathroom and I'll show you."

"How about I let you take that little trip yourself."

"Too much masturbation can lead to night blindness."

"What do they consider too much?"

"That's a good question. Since a man made the rule, my hand would most likely fall off before night blindness set in."

"So I think you're safe to go at it alone."

Jess stood still for a moment, gazing up and down Rory's body.

She blushed. "What are you doing?"

"Just getting a mental image."

Paris grabbed Rory's arm, pulling her away from Jess. "Let's go to the library, Rory."

Jess gave her a little wave. "Bye Rory."

* * *

"You have to stop that." Paris huffed.

"I have no idea what you're talking about."

"You're practically sleeping with the enemy."

Rory looked annoyed. "I'm not sleeping with Jess."

"You gave him masturbation material."

"I was just having a little fun."

"Fun time with Jess is over."

"Paris, nothing is going on with Jess."

"That's not what it looked like to me. You were blushing. He made you blush."

Rory put the brakes on any more talk about Jess when she noticed her perfect blonde haired boyfriend making his way toward her. "Oh look, here comes Logan."

"Yes, here comes Logan, your boyfriend. Jess' best friend."

"Drop it, Gellar," Rory muttered, through clenched teeth. "Not another word or everyone will know about you and your cousin."

The best bitches always kept one secret about their enemies in case of emergencies like this.

If Chilton knew about Paris and her cousin, she'd never be Bonaparte again.

Kissing cousins hadn't been kosher in high society since the British stopped openly inbreeding.

"He's my second cousin," Paris muttered.

"You really think that will matter to anyone at Chilton?" Rory gave her that cold, emotionless smile she had perfected upon exiting her mother's womb.

Rory Gilmore was born a bitch.

Anyone with common sense would wonder why Paris Gellar even associated with someone who dangled secrets over her head like a carrot to a horse, but in this world, the Godfather mantra truly did apply.

If you're not sleeping with the enemy, at least make sure you're making small talk to their face, with that butcher knife twirling in your hands behind your back.

And one day when she turned around, it would be the death of her.

All this talk of murder is a bit unsettling, girls. What happened to putting your rivals bra in the freezer and sleeping with her boyfriend?

It must be too been there, done that for this set. And that is meant in the most literal sense. You can only do someone so often before it becomes mundane.

"Ace, love of my life, where have you been all morning?" Logan laughed at himself. Or with himself.

Everyone else just laughed at his pathetic attempt to be humorous.

Rory didn't even smile. "Are you drunk already?"

"What, no kiss good morning?"

"In case you forgot, we're not getting along at the moment."

"I've forgiven you."

"Really, you forgive me Logan?" She delivered this in an overly sweet tone of voice that let Logan know he was still on her shit list. "Gosh, I'm such a lucky girl to have a boyfriend that fucks around and forgives me, aren't I Paris?"

"How I wish I was you," Paris mumbled, knowing she had to play along.

"You're still mad about that?"

"Still mad? STILL MAD? You're lucky I'm not completely insane or you'd be missing your favorite member."

"I sleep with one eye open for a reason," Logan responded, almost in a whisper.

Rory sighed, popping a piece of gum into her mouth. She leaned in close to Logan, close enough to kiss him, kill him or whisper to him. "Enjoying fucking yourself tonight."

"It's not like you ever would."

"It's not like I'd ever want to."

"What, you're going to go off and fuck Jess now?"

"I'll start with Jess, then work my way around. By tomorrow I should be done with the entire junior class."

"Good luck with that," he spat out bitterly. She was a pro at getting to him.

She popped a bubble in his ear. "You know you love me."

She spun around on her heels, making the perfect exit.

She might cry alone in her room over Logan, but he'd never know it.

No matter how many times she taunted him, emasculated him or threatened to fuck his best friend, Logan continued to come back for more.

They were the definition of a fucked up match made in heaven.

Paris Gellar had disappeared during their little battle. She probably went off to stick another needle in her Rory voodoo doll.

It was equipped with a headband and faux leopard coat (even the insanely rich had a soft spot for animals, if you weren't an Olsen twin). Quite life like. They were all the rage at Chilton, especially among those that Rory made quiver with fear.

Translation: everyone.

* * *

Miss Fischer was the epitome of everything no Chilton girl wanted to be. She wore department store Mary Janes, sported eyebrows that would dethrone Peter Gallagher and insisted on reapplying a whorish color of lipstick everyday in class.

Rory pitied her.

At least she had nice cheekbones.

"Jess, how did you feel about last nights reading?" Miss Fischer was in love with Jess. Pretty much every female staff member had a diary entry or two about how much they loved Jess Mariano.

His ability to charm the female staff was why he passed chemistry. And geometry. And any other class he had taken since he had hit puberty.

Miss Fischer always called on Jess just so she could openly flirt with him without raising the suspicions of Headmaster Charleston. It didn't matter what Jess replied with; Miss Fischer was always one smirk away from having to excuse herself.

Her cheeks had already turned a dangerous color of pink. The poor woman was _struggling_.

He smiled, removing his eyes from Rory's thighs.

Rory's skirt was three inches shorter than dress code required, but not even Charleston would fight with her over how much leg she showed off to her male peers.

"Saroyan was a Hemingway wannabe." That's right ladies and gentleman; dickhead had a brain and used it from time to time, when he actually made an appearance in class.

Rory rolled her eyes. She knew Miss Fischer would be useless the rest of the class period, too busy writing 'Miss Fischer Mariano' in her grade book.

"Hemingway was just a depressive drunk who was jealous Saroyan was better than he was." Rory lived off of starting confrontation. But she did have an extreme distaste for Hemingway.

"Saroyan went on and on about how he was the greatest writer of his time, but what does he have to show for it? No one knows who the fuck he is now."

"Language, Jess," Miss Fischer warned. She wasn't even taking part in this soon to be lively debate.

"It's pathetic that people would rather read an entire book about fish than 'The Time of Your Life.'"

"It's about more than just a fish."

"The entire book is about his struggle to catch this giant marlin. Who cares? It's just a fish."

Jess stifled a laugh. "You're supposed to be Miss 2300 on her SAT's right? How could you not get the symbolism? The marlin is more than just a marlin."

"Jess, don't insult Rory's intelligence. She's entitled to her opinion."

"Miss Fischer, I'm just simply enlightening her."

Rory interjected, wanting to piss Jess off even more. "It was 100 pages of wasted symbolism."

"So are you implying that _Moby Dick _was a waste of paper?"

"You can't compare Melville and Hemingway."

"Both _Moby Dick_ and _The Old Man and The Sea_ have biblical symbolism. Both are a about a man out at sea."

"Melville didn't compare himself to Jesus Christ. You're just a fan of Hemingway because he enjoyed booze and bar fights."

"So did Saroyan. In fact, Saroyan and Hemingway were known rivals."

"But Saroyan was not a Hemingway wannabe. You can't really believe that."

"I can believe whatever I want, sweetheart."

"What did you just call me?"

"It's a term of endearment."

"Take that back."

"Would you prefer I called you something else? How do you feel about Freckles?"

"I'd prefer if you didn't give me a nickname."

Miss Fischer cleared her throat. "Lively debate you two. Does anyone else have something to add?"

Paris Gellar raised her hand. "Yes, Miss Gellar?"

"Can we start a petition to have these two locked in a room so they will be forced to sort out their issues?"

"Paris!" Rory practically squealed.

"Sorry Gilmore but every day it's the same thing. You two bicker over the literature, then end up fighting about Jess staring at your legs or him giving you a nickname or how many times he said your name to condescend you. It's ridiculous. I'm here for an education; not to listen to you two idiots flirt over Saroyan."

"We weren't flirting!"

"Rory, stop yelling at Paris," Miss Fischer interjected.

"Yes Rory, calm down. You don't want to get sent to the office again." There was Jess, condescending her again.

"That was once and it was your fault. You bumped into me on purpose."

Finn lifted his head from his desk, pissed that Rory's squealing had stirred him from his slumber. "Love, if you don't keep it down I'll be the first one to sign that petition."

"Go fuck Colin," she spat out, that famous Gilmore rash forming on her neck.

"No need to bring Colin's ass into this, love. It's not my fault you use your mouth double to make up for not making use of other parts of yourself."

"I have no clue what you're talking about."

"I'd be happy to give that part of you a little action."

"Finn, don't talk about Rory's innocence like that. You don't want me to call Miss Fairfield in here, do you?" Miss Fischer threatened.

Miss Fairfield liked three things: Jesus, Jude Law and show tunes, in that order. Everyone was pretty sure she was asexual. Actually they weren't even sure if Miss Fairfield was a woman. It was still a mystery not even Jess had figured out.

But whenever a girl's innocence was brought up, Miss Fairfield was dragged into class to give everyone a lecture on how everyone only had one toothbrush and now everyone but Rory had a dirty toothbrush.

Her metaphors were truly inspired. And quite graphic.

Jess groaned. "We all know Rory only has one toothbrush. We just think she'd be better off if she let one of us borrow it."

"We promise to give it back," Finn fretted.

"In five to ten minutes." Jess adjusted his tie, stealing a glance at Rory's perfectly pink ears.

"What do you say, love? Broom closet before history?"

"Fuck off," she muttered, sick of her virginity being topic for discussion everyday.

"Miss Gilmore, language," Jess said, mocking Miss Fischer.

The bell rang, releasing Rory from her own private suicide.

Jess made sure he brushed up against her when exiting the classroom even though it was ridiculous to think her 90-pound frame took up any space.

"Fun as always, Gilmore," he breathed into her hair, lingering for a moment to take in her scent of cinnamon and patchouli. "My offer still stands."

Rory whipped around, so close to him that her hair slapped him in his face.

Once again, their lips were centimeters apart. But Rory wasn't in the mood to linger.

"From now on, don't talk to me…."

"You don't mean that. You like when I pay attention to you. When I accidentally brush up against you. You like our little debates over Hemingway. They get you going."

Rory huffed and pushed her finger into his chest. "Shut up! Did I say I was finished? Don't interrupt me with your little psychoanalysis. Don't talk to me. Don't look at me. Don't even say my name. In fact, don't think about me. Leave me the fuck alone from now on."

He removed her finger from his chest. A visible anger had washed over his features. "As you wish, Princess."

"Don't do that."

"Do what?"

"Act like you know me. You know nothing about me."

"O-k-a-y." He took the time to pronounce each letter.

"You're infuriating!"

He leaned in closer, almost whispering in her ear, but instead, leaving his hot breath on her cheek. "Does Logan get to you like this?"

"He's your best friend," she whispered, almost like she didn't want to say that. Almost like she didn't want to say anything.

Look who was struggling now.

"Hoes before bros." He couldn't be cute forever.

She pushed him away from her, finally, after the longest thirty seconds on record. Call Guinness.

She was too flustered to think of a witty retort. She brushed a strand of hair out of her eyes before Jess could push it behind her ear. She wasn't letting him get _that_ close.

She started backing away from him, gathering her books as he stood there seemingly unshaken, smirking.

"This…never…happened. I don't know what's wrong with me." She released that last part in a bitter tone, a tone that was meant to be hurtful, like why in the world would she ever associate with the likes of _him_.

Check mate for Jess Mariano.

* * *

There was a reason we as humans walked forwards instead of backwards.

When we stumbled backwards, we tended to run into people. And sometimes, we'd run into that one person we'd hoped had died in a tragic something or another. Suffocating on cotton candy would suffice.

Rory Gilmore, lacking the grace a future debutante should instill, slammed into that one person she had wished some type of tragic death on (not that Rory would weep over her).

"I'm sorry, I'm sorry, I'm sorry..." Rory knew that voice, that need to apologize. It was Bambi with wolf's fangs.

She slowly turned around, praying she had misheard. Praying it was just some squeaky freshman.

It wasn't.

Their eyes locked for a moment before E lunged at her. For a hug, not to strangle her.

E was not the one with anger issues.

That urge to vomit E regularly caused hit Rory again.

"I'd missed you so much," E gushed like they were still best friends.

"Yeah." Rory awkwardly untangled herself from E's hug and stood up, forgetting about the books and papers littering the floor.

She couldn't let anyone think they were friends again.

"I didn't know you were back," Rory lied.

"Daddy and mommy Warbucks got sick of me."

"Shocking."

"But now I'm back! I'd missed you. No one is as much fun as Rory Gilmore."

"I have to go," Rory said, abruptly ending the conversation.

E made her signature puppy dog face at Rory that had gotten her in more trouble than any boy ever could. "Aw, so soon?"

"Harvard prefers you to not spend a year in France sucking down champagne and sleeping with princes. And to attend class. Which is what I have to do." She showed E her watch as some kind of collateral that she really did have to leave. "I wish I could stand here and catch up, really I do, but..."

"You never did lie well." E popped a bubble right in Rory's face. Strawberry gum. She always smelled like strawberry and weed.

"We should get drinks later." Why was Rory offering to voluntarily hang out with her? What was she plotting?

"I'd like that. And bring Lorelai."

"She's busy." Lie, lie, lie again Pinocchio. Your nose might start growing one of these days.

"That's a shame; Lorelai is so much fun."

"Yeah, a shame. Look, I really do have to go."

"Is Logan waiting for you?"

Rory stiffened at that question. She hated when E mentioned Logan. "No. Coffee is."

"Well don't let me keep you from your one true love. Besides, I see Jess. He's always fun."

"That's what his card says." Rory rushed off, leaving behind all her dignity.

Audrey Hepburn would not be proud.

Drinks with E later? That was the recipe for a classic society cat fight.

Let's hope someone has a camera phone on hand.

* * *

**Ending Author's Note**: Nothing about the story yet but if you haven't checked it out, go watch the awesomeness that is Dr. Horrible. The link is in my profile page, along with a little fangirl rant. But it's hysterically awesome.

No name for Miss E yet. It'll come in due time. Think of it like the mystery of janitor's name on Scrubs. Maybe it'll become like my thing to not give characters whole names! It'll be our thing, like the bridge for Rory and Jess. Yeah, that's tight.

William Saroyan, if you don't know, is this awesome author that no one knows about (probably why I prefaced this with no one knows) who I took a semester on. So google him just for the hell of it, please. And yes, I kept Rory and Jess all book loving cause the characters must have depth! Except for E. Gotta have one person who is superficial somewhere. The world is full of them (that's why we have plastic boobs everywhere).

**Reviewers**: If I was able to, I'd hand out 20 dollar bills to yah'll like Frank did at the Sands. Sadly, I can't pay you off. So I guess I'm asking you to be my story whores for free.

There are worse offers out there, right?

But yeah do that review thing with jazz hands, cartwheels and gushing about moi.


	3. You're Supposed To Be My Friend

**Chapter 3: **You're Supposed to Be My Friend

**Author's Note**: None of you live inside my head (thank god for that; my head is like a freaking snow globe that never stops shaking) but I like to post a chapter a week, so my almost extra week long delay has been causing me all kinds of inner turmoil. And then last night, while I was finishing up the chapter, it all disappeared. I cried for like half a minute, then realized my memory wasn't that good and tried to rewrite it all. It's not the same, but since you didn't know what it was prior to the computer death, you'll never know which was better (insert evil laugh here).

This title is not dirty. Sorry folks! I did think of an alternate title, but it was a little too blunt for my lovely T rating which I might end up changing if I don't stop talking like Satan's offspring. I do love using the word fuck it appears. Oops, I said it again.

**Disclaimer**: I own my awesomeness. And I guess I now own E, since I finally gave her a personality, minus the name. I just love not naming people. Feel sorry for my nonexistent kids.

* * *

The lunchroom at Chilton was like any other cafeteria at any other high school. Pretty people ate with pretty people (and then went to the bathroom to throw up).

The band geeks huddled in a corner and cried into their tubas.

The freaks did what freaks do. They ate their own hair, picked at each other like monkeys at the zoo and plotted an attack on the Hartford Boy's Club that involved forks and black hair dye.

Ah, the Hartford Boy's Club. How does one begin to describe them?

It consisted of, at this moment, four obscenely charming assholes.

Just a month ago, Tristan DuGrey was a part of this elite group, but an incident with Rory's panties and her subsequent verbal castration of him led to him going into hiding, a la Michael Jackson minus the umbrella and glove.

But more on that later.

You could probably guess the other four douche bags without any help. All but one were devastatingly handsome. All were born with silver spoons in their mouths. All were the object of every girl's affection, except for Paris Gellar but only because she preferred men twice her age.

But can you blame a girl for wanting a man, not a boy?

They supposedly took part in some secret underground club that was rumored to be called _The Life and Death Brigade_. Rory referred to them more lovingly as the BSB gang.

Don't rush out to buy your front row seats for their world tour just yet. Rory only used those three letters to come up with a name because she liked that it suggested that Brokeback type things went on in the showers between the four after soccer practice (which might be true if you listened to Finn when he was drunk). Also, who didn't giggle at the imagery of those four dancing in the rain with their hands over their hearts?

But when referring to the HBC, those three letters stood for "Ball Sucker Boys."

Now there was a term of endearment for you.

Basically the four went around town taking part in a less graphic, less illegal version of _The Clockwork Orange_. They wore mask, drank Grey Goose and liked to jump off of things that were vertically much higher than them.

If you wanted to see the effects of weed on the brain, just do a case study on these four.

But their favorite activity, that didn't involve smoking or getting blown, was sitting around the lunch table rating the finest Chilton asses (the boys bathroom wall was quite an informative piece of concrete) and talking about how awesome they were.

Today was no exception. And guess what lovely Chilton lady was the topic of discussion?

* * *

Finn liked to use his hands when he spoke. It was annoying, a little gay, and dangerous for low flying birds and midgets.

Watch out Oompa Loompas!

"So then I offer to dirty up her toothbrush a bit, and bloody hell, she looked like her head was going to explode!"

Colin was still a bit distraught that Rory thought he and Finn liked to look at each other in the shower. "She told you to fuck me? Why not yourself? Why me?"

Jess shook his head. He wasn't really taking part in this conversation, still stuck on how flustered Rory Gilmore was. It was a bit mind blowing to know he had that effect on Chilton's princess.

"Colin, you're known as the ambiguously gay duo. Get over it." Only the truth should be bothersome, right? Colin should have nothing to worry about if he didn't fancy Finn's behind.

"But I banged Jennifer Waters just last night," he whined, making a case for his heterosexual ways.

Jess rolled his eyes. Colin was seriously acting like a brilliant retard, if that made any sense. "Everyone has banged Jennifer Waters. Half the girls here have probably done something _Girls Gone Wild_ worthy with Jennifer Waters."

Colin blinked, "You've all banged Jen?"

Finn and Jess smiled, shaking their heads at their stupid friend.

"So we've all fucked each other?"

Jess shook his head. "If you believe the bible and Miss Fairfield."

"This blows."

"Hey, at least Jen is experienced. And she's insane. She does all that weird shit without even having to make a trip to Tiffany's." Jess had made one too many trips to Tiffany's to seal the deal. Colin should consider himself lucky he didn't have to shell out thousands of dollars for Jen to take off her panties.

Finn nodded his head, remembering his brief encounter with Jennifer at Rory's sixteenth birthday party. "She's like that freak from _The 40 Year Old Virgin_."

Colin chugged his whole can of soda, suddenly feeling like he needed to pass out. And go get a cream for the crabs that were sure to appear. Soon.

Finn swung his hands around, almost slapping Jess in the face.

"Watch the hair!" Jess swatted his hands away. His hair was his temple. He really needed to install a plastic bubble around it.

"No one cares about your hair, pretty boy. But let me finish my story about the lovely Rory."

"I was there."

"But Colin wasn't."

"Colin is lost. He can't handle that we've all fucked each other."

"If I had to fuck a guy, I wouldn't mind it being one of you." The bromance never stopped with Finn.

"Same here. You're an attractive man, Finnegan."

"I admire your ass, Mariano."

"So does Rory," he responded, all wiggly eyebrows.

"Ah yes, the lovely Rory. I don't know how this man does it," he pointed to Jess, "but he knows exactly what buttons to push."

"I tried to pay attention in anatomy."

"Do you and Gilmore have a thing or something?" Colin asked, brought out of his STD fueled trance.

Jess went white, but just for a moment. Play it cool Jess. Play it ice cold. "Me and that frigid bitch? Nah, I just like watching her squirm."

"I think she has a thing for you." Finn had heard about the infamous nose graze from Lorelai's party. Well, actually, now the gossip was that Rory was groping Jess under the table at dinner.

Close enough to the truth, right?

"Who has a thing for Jess?" Logan was always late for lunch. From 11:40-12:00 everyday he was busy getting acquainted with a different cheerleader from the Chilton cheer squad. They were all so eager to please. Peppy you might say.

They sure did make Logan cheer.

All the boys froze. It was the classic deer in headlights look. Or the classic 'I'm about to shit myself' look. Either way, none of these normally chatty fellows had much to say.

"Enjoy your lunch?" Finn asked, trying to get Logan off track.

"It's not much of a lunch for me. I'm starving."

"I bet Miss Pom Poms is full," Jess quipped.

"Have you done Jennifer Waters?" Colin asked, out of nowhere. He was still stuck on that slut?

Logan rolled his eyes at Colin, the tagged virgin of the group, even though Colin had lost his virginity when he was twelve in Amsterdam.

"Everyone's done Jennifer at least once."

"Colin just did Jennifer for the first time," Finn pointed out like it was news worthy of throwing a parade for him.

"How was it? Did she do that thing with her legs?"

"She's so flexible. It's like doing it with a Russian ballerina." Finn liked the girls who could put their legs behind their head. But really, who didn't? Missionary was so 1950s.

"Is Rory that flexible?" Was Jess looking for a duel? Did he want to start a fight with his best friend?

Finn laughed. "It's common knowledge Rory is saving herself."

"For a bigger penis." Colin was actually not comatose when it came to penis talk.

"Seriously Logan, why haven't you tapped that yet? The girl has got to be a freak in the bed. She's borderline insane." Finn tapped anything, even if they were just released from the asylum. The freakier the better was his motto. Let's just hope he got the girl tested before he showed her the goods.

"She's a psycho." Colin, like any other sane person, was a bit afraid of Rory.

"But she's got killer legs, so the hot/crazy scale is kept in balance." The hot/crazy scale was Finn's bible. He consulted it for every pair of legs he was stuck on.

Logan searched his pockets, looking for a reason. "Rory…she's different."

"Aw, you think Rory's special?" Jess said this in that baby talk sort of way that made Logan clench his fist.

In this moment, he really wanted to beat the shit out of his best friend.

"You do any other girl, more than one girl a day sometimes. And yet you haven't gotten Rory to give it up in four years? Something is wrong there."

"Jess, Rory's special," Finn mocked.

"It's not my fault. She's the one who is all about waiting. No one could get her v-card out of her."

Jess smirked. "Is that a challenge?"

"Uh no, that was a statement."

"Is there something wrong with Rory?" Colin wanted something to hold over Rory's head for all the times she had made him cry. Aw Colin, your poor sensitive little bastard.

"Is she a closet lesbian?" Finn was all about the girl on girl action that he didn't have to pay for and he was pretty sure he could install a peep hole in Rory's closet. And wait.

"Did she laugh at your penis?" If she laughed at Logan's, you might not want to get between her knees, Jess.

"Why do you all care?"

Finn slammed his hands on the table, like this was some official mob business. "Because it's your right to be having steady sex. We're just looking out for one of our own. You should at least be getting blowjobs. Tell me you're getting blow jobs."

Logan tossed his head back in a painful laugh. "Rory give a blow job? She might get her Chanel dress dirty."

"And Audrey Hepburn doesn't give blowjobs in Roman Holiday," Jess added, forgetting that he was revealing that he knew a bit more about Rory Gilmore than he should.

Logan cocked an eyebrow at him. "How do you know about Audrey Hepburn?"

"Her and Jess bicker everyday in English. It probably came up during one of their fights."

"You talk to Rory?"

"I wouldn't call it talking. I just piss her off about Hemingway or Austen or E.E Cummings when I want to be inappropriate."

"You read?'

"It's why I'm such a brilliant orator."

"I didn't know you were gunning to be the white Barack Obama."

"The ladies go weak in the knees for a well spoken man."

"Or a man with an accent," Finn added, laying the Australian slur on thick.

"I had sex with you, and you, and you," Colin stated in a trance, pointing to each boy and shaking his head in shame.

"Ignore him; he's having trouble with the concept of what a slut is."

"Maybe you should define it for him since you are the great mind of this group."

"Slut: A person with a healthy sexual appetite who might test positive for a few pesky things."

"Could you use that in a sentence?"

"Logan is a slut."

"You're one to talk."

"I'm not branded by Rory Gilmore, therefore, I'm just an explorer. The Columbus of vaginas." He stopped for a moment, deciding, why not be a slimy little bastard? "I'm surprised Rory puts up with your manwhore ways."

"Is there a roadblock to Rory's vagina?" This was of great concern to Finn because one day, Rory would kill Logan and he would slide in to comfort her. The HBC were some loyal friends. Never leave a man's woman a virgin.

"Does her mom have the key to her chastity belt?" No Jess, Emily did and she certainly wasn't going to give it to _you_.

"Do we need to pull a Mission Impossible and get it for you?" Finn in all black. Yum.

"Rory isn't like all the other girls at this school."

Jess rolled his eyes. "We know; she has morals."

"No, she's just…if you fuck Rory Gilmore, it's a big frickin deal. That's it. You're stuck with her. With Rory, everything is a big thing."

"Is there going to be a banner on her V-Day?" Maybe you can make it, Finnegan.

"Maybe Rory will decide to live the celibate life," Colin mused, because in his mind, who would want to fuck that? Not even a Grizzly Bear would test the waters of Rory's vagina.

"You can't let an ass like that go to waste, " Jess reasoned.

"There are a lot of hot nuns. I hang out at convents all the time."

Logan laughed at one of Finn's many odd fetishes. "You're so messed up, man."

"Horny is the word for it. I haven't had a decent lay in months. Maybe I'll give Jennifer a call."

"Shut up, Finn," Colin groaned.

Jess wiped his eyes, tired of this conversation. He had better things to do. More stimulating things.

And no, he didn't mean a girl, although that was normally stimulating for certain senses.

"I've gotta go guys," he said, taking one last swig of his soda.

"Where are you rushing off to?" Logan was trying to stall him. He wanted to play a little good cop/bad cop on his friend about what was going on with Rory.

Jess grabbed his blazer off the back of his chair and swung it over his shoulder, backing up as he spoke. "I've got tutoring."

"Bullshit," Logan said.

"Boys scout's honor. I'm going to get a little help in math."

"What's her cup size?" Finn quizzed him.

"I'm appalled you guys don't think I'm just trying to advance my education," he paused, a devilish grin adorning his features.

That'd sell it. "And they're D's."

"Excellent," Logan applauded his friend.

"Nice work, mate. Full report tonight at my house. We'll do poker and cigars. Father got these Cubans that are bloody brilliant."

But Jess had already disappeared.

But not to go get a little help in math from some D cupped fantasy.

Jess didn't need help in math. Or any other subject. If he applied himself at all, he'd be considered a boy genius.

Nope, Jess Mariano was off to find his new favorite game, Miss Rory Gilmore.

* * *

Rory clinked her glass with E's, a wicked smile adorning her Snow White like features. How could someone so innocent looking be so bad?

"Best friends forever." E took a sip of her martini, then fished out the olives and shoved them into her mouth.

"Forever." Rory's eyes glimmered when she said that word. Forever was quite a long time for her to be professing her friendship to a girl who had ruined her life, according to her diary and therapist.

Suddenly, E grabbed onto the table, trying to find balance. Her regularly tan face had gone the color of Rory's perfectly ivory skin. She put her hand to her forehead, checking for a fever.

"I don't feel so well."

"Really? That's a shame. Maybe you should go lie down." Rory took another sip of her martini, not even offering to fetch E a cab.

E tried to stand up but quickly sat back down when she realized the room wasn't actually spinning.

It was her.

"What's wrong with me? I feel so hot."

"I poisoned you." Rory tossed a handful of peanuts into her mouth and wiped her hands on E's glittery mini dress.

"You what?"

"When you went to the bathroom I slipped something into your drink." She pulled out the vial, now empty. This must have been the prestige part of her magic trick; show E how she killed her. That was definitely something she had never seen before.

At least we hope so but when you're friends with Rory Gilmore, who knows how many times she has tried to kill you.

"Why would you…" E began to cough, her little body shaking violently. Rory just continued drinking her martini, patting her friend on the back to show the other customers that she cared.

"Why would I kill you? Well, you probably won't be conscious long enough for me to explain it to you, so I might as well get to the point. I hate you."

"You're such a…"

"Bitch? Yeah, but you already knew that."

E hit the floor, her blonde hair covering her soon to be dead face.

Rory flagged down the bartender. "Can I get another martini?"

"What about your friend?"

"I think she's had enough."

"One martini and she's on the floor?"

"She never did handle her alcohol well."

She pulled her Too Faced Mood Swing lip-gloss from her purse, applying a fresh coat.

Killers still had to look hot, especially in high society. And this killer was all about cruelty free lip-gloss, even though she didn't exactly abide by that rule in the social world.

The real question was what color would her lips take on? Was she happy?

Obviously.

Hot and bothered?

Did we miss Jess' appearance?

Was she jealous?

Of a dead girl? We think not. Corpses have never been hot.

Out of nowhere, Logan popped into the seat beside her, stepping right over E's body. He was outfitted in a Burberry trench coat and fedora.

Odd choice of outfit, Mr. Huntzberger. He was aware he was not Humphrey Bogart, correct?

"You killed E, I see." He didn't seem too bothered by the death of the girl who had deflowered him.

Rory choked on air. "You're crazy."

"I'm not the one who's drinking martinis with a corpse."

"I'm a Gilmore."

"Precisely. Gilmore's are known for their tempers followed by irrational behavior."

"It's not like anyone will miss her."

"You're right."

"I'm what?"

"She's better off dead."

Rory looked around the room, searching for Ashton Kutcher and the Hartford police department. This had to be a set up. She had been caught. And her boyfriend of four years was in on the bust.

Stop. Think clearly. She was a Gilmore. Gilmore's didn't get…

Logan leaned in, capturing Rory's bottom lip. He moved his mouth against hers in a kiss more passionate than anything they'd ever shared.

He pulled back, leaning his forehead against hers. "Murder turns me on."

"I'm confused."

"I love you, Rory Gilmore." He kissed her again, this time sweeter, briefer. This time it was less likely to be a ploy to keep her from running. "You can be the Bonnie to my Clyde."

"What'd you do? Knock off a bank?"

"I killed Jess."

"Why?"

"I never liked his hair."

"Now all our problems are gone."

"And we can be together."

"Forever," she whispered, almost like she couldn't believe this was happening.

She felt a hot liquid on her lap. Had E risen from the dead and bled on her Ralph Lauren sweater dress?

She looked up and locked eyes with those awful chocolate pools her grandmother detested.

Wait, wasn't Jess dead?

He smirked. "You need to take off that skirt before the stain sets in."

Ugh. She had been day dreaming, yet again.

Rory really did live in a dream world. One fucked up dream world.

"You're supposed to be dead."

He clutched his chest. "It's all fun and games until Gilmore spills her coffee. Daydreaming again? Where were we this time? In Charleston's office?"

"You're perverse."

"I think we could have some fun on his desk."

"He has a stapler, right?"

"I suppose. Why? Looking for something kinky?"

"Why, does a staple through the penis get you going?"

"I knew you had sadist tendencies buried underneath all that sexual repression."

She stood up, letting the coffee drip off her skirt to the ground and headed in the opposite direction of wherever Jess was headed.

Too bad for her he was headed in her direction.

"Stop following me."

"I'm not following you. I'm trying to help you."

"I can get rid of a stain on my own."

"I'm great with laundry."

"Good luck with that as a profession."

He jogged a bit to get in front of her, stumbling backwards so he could keep his face on hers. "Why do you always run away from me?"

"People tend to run away from their stalker."

He laughed, brushing past a group of girls who were more than happy to run into Jess Mariano. Too bad for them he was solely focused on Rory Gilmore at the moment.

"Maybe you're stalking me."

"I was at that bench first."

"I was in class first."

"We share the same class. I have to be there."

"And so do I. And I happen to enjoy coffee. It's not my fault the coffee is beside your bench."

"But you know I love coffee!"

"It's not my fault you have an unhealthy relationship with caffeine."

"And at my mother's party…" She trailed off, not really having a leg to stand on.

"You walked up to me. You fixed my tie. You lingered."

"Don't use that word."

His back hit a door and he realized he had made it to the girl's bathroom without her killing him with the death rays she tended to send to anyone in her presence.

"Oh look, the girl's bathroom. And you have a stain. And the bathroom has water and soap. It's fate."

"It's a bathroom."

"I think I should help you."

"I can take care of myself."

Rory pushed her way past his very annoying form, sending the swinging door into his face.

She called back out to him, in a taunting manner, thinking she had won. "And unless you have a vagina, you can't come in here."

But the lack of a vagina wasn't going to stop Jess Mariano. He rubbed the spot on his head where a bruise was likely to form and walked into the girl's bathroom.

"I can't read," he stated smugly, still rubbing his head. "You play rough."

"Get out," she said this calmly, because in all honesty, his presence didn't bother her.

"I'm in here more often than you are. By the way, never use stall number two. No amount of Clorox could clean that one up."

"You're gross, really."

"Why thank you, dear."

He pulled a few paper towels out of the dispenser, and ran them under water. Walking up to Rory, he got down on his knees, his hands resting on her hips.

"What are you doing?"

"You talk too much. Just trust me." He started scrubbing at the coffee stain on her skirt, holding the only material that stood between seeing Rory's panties in his hand.

"If someone walks in here…"She tended to lose her words when it came to Jess since the nose graze fiasco.

Right now, she was losing her mind.

She shouldn't be letting him touch her like this. But he was being so sweet. His intentions seemed honorable. He was her knight in shining plaid at this very moment.

Pure evil had never taken such a romantic form.

"Then someone walks in here. I'm getting a stain out of your skirt, right?"

She gulped. "Right."

He scrubbed for a bit longer, then stopped, staying on his knees for a few moments, one hand still lingering on Rory's hip.

She studied the placement of his hand. He could have moved it lower. He could have tried something as he was scrubbing away. "Why are you being nice to me?"

He stood up, tossing the paper towels into the trashcan. "Why'd you let me help you with that stain?"

"I don't know." She looked away from him.

He took a step closer, knowing it would make her more uncomfortable, knowing that he could have her skirt bunched around her hips if he said the right words.

"You could have pushed me away. Shoved me into the wall. Bit me."

"I haven't bitten you since we were three."

He ignored her attempt to kill the moment. "But you didn't."

"You didn't answer my question." She chewed on her lip, nearly drawing blood.

"You didn't answer mine."

"I asked first.'

"Semantics, Freckles."

She couldn't stop the smile that hit her face with that dreadful nickname.

He moved a bit closer, close enough that she could feel his breath on her cheek. He locked his eyes on her lips, his mind already wandering to what her lip gloss would taste like. How her soft pink lips would feel against his. Would her peppermint gum accidentally slip into his mouth. Would he give it back?

Right now, her mood was definitely hot and bothered with a splash of dare we say, happy?

"I'm going to ask you something else."

"Okay." She knew what he was going to ask. Her hands were trembling at her sides in preparation for what she was going to let happen.

"How would you react if I leaned in right now and kissed you?"

The moment, her answer, the possible outcome was all ruined by a scream. "Jess Mariano, get out of the ladies bathroom!"

You could always count on the Dean of discipline to ruin anything for Jess Mariano. Dean Hessler hated him simply because Jess took away all the attention his thirty-two year old ass should have been receiving from the female students.

It was common knowledge that the Dean had slept with a few of Chilton's finest.

It must have been hard to avoid his boyish good looks. That or the Daddy figure thing really was popular among the seriously messed up.

"Seriously," he muttered under his breath.

Rory had been saved. For show, she gave Jess a little shove. "Yes Jess, get out of the girl's bathroom!"

She walked past him with a fake look of disgust plastered on her face. "Jess is out of control, Dean. Something must be done."

"I'll look into it, Miss Gilmore."

Jess couldn't help but laugh at Rory's attempt to save face.

"Something funny Mr. Mariano?"

He turned around. Rory had already left the bathroom. He noticed the Dean's eyes were following her behind.

The Dean had a thing for Rory.

Someone needed to tell him to give up on that fantasy. Sleeping with the dean of discipline was not even on Rory's radar. Plus, it held a serious ick factor. He had graduated from UCLA and wore L.L Bean pants. Ew.

"She does have a nice ass."

"I beg your pardon?"

"It's just us boys now, Dean. You can admit that Rory has a fantastic ass."

"Do you want me to suspend you?"

"I've been wanting to take a trip down to Brazil. It's bikini season," he gave the Dean that smile that he hated more than Jess speaking.

The Dean smiled. "I wouldn't give you the satisfaction of a suspension."

"Then what are you going to do with me?"

"You'll see, Mr. Mariano."

"Do you want me to give you a play by play of what went on with Miss Gilmore? Sorry, but I don't kiss and tell."

"I'd advise that you don't say another word about Richard Gilmore's granddaughter, Jess."

"How does Richard feel about your admiration for Rory's ass?"

The Dean turned a deep red. His head might explode at any moment. He grabbed Jess' tie, dragging him out of the bathroom. "I really hate your kind."

"That's a shame because I love you so much."

"Sarcasm, how original."

"I try my best."

* * *

It was best not to mix blind rage and alcohol. It didn't matter if you ordered the new concoction shaken, not stirred; the results were never James Bond smooth. It tended to make you say things, do things or act in ways that a Chilton Princess shouldn't.

Think sleeping with your boyfriend's best friend. Doing lines with a boy with no trust fund that probably rode a Harley. Ripping the golden locks from your ex-best friend's head in front of everyone, even the _New York Post_ page six writer.

Hair in the martins certainly wasn't good for business unless the two girls ended up with their tops off having it out in the water fountain in the lobby. Maybe Rory should stop with the alcohol. Or take a valium.

Another thing Rory Gilmore shouldn't have done was arrive at the bar at the hotel her mother owned/pretended to run thirty minutes early. Thirty minutes was enough time for at least five martinis. Five martins would make her ninety-pound frame slur her words and make out with inappropriate people.

It was a good thing for her Jess Mariano was not lurking in the hotel lobby.

Rory had pulled her hair into a severe ponytail, and hadn't taken the time to change out of her coffee stained skirt; but because she was a high society goddess, she still looked flawless.

But, she should not make it a habit of showing up looking like a girl who was only at Chilton because she was on scholarship.

If her new look was going to be sweat pants and stained clothes, she should at least save herself from the embarrassment and stay in bed until she sorted out whatever was bothering her.

She looked down at her cell phone. E was fifteen minutes late.

E's Mad Hatter like tendencies were endearing when Rory actually liked her. But now, when she'd love nothing more than to rip every single hair from her head, E's lateness just made Rory grip her martini glass even tighter.

_Watch out Rory. Glass breaks easier than E's neck._

"What's so special about her?" She mumbled to herself. As long as she wasn't expecting an answer, it was safe to say she hadn't gone completely mad.

"About who?" E asked, her blonde hair hitting Rory in the face as she slid herself into the booth, cuddling up next to Rory.

Rory took another sip of her martini, already having to force herself to fight back the desire to slam E's head into the table. "You're late."

"I'm always late."

"It's not one of your endearing qualities." Not that she has any, according to Rory.

"I'm sorry, Miss Punctuality. You know I hate clocks."

"You're sounding stupid."

"What's going on with you?"

"What are you talking about?"

"You're being more of a bitch than you usually are."

"I've been waiting for forty-five minutes."

"Then I guess you're sufficiently hammered."

"At least I wait until five o'clock."

"Are you unhappy to see me?"

"Oh if you only knew."

"Jess is right. You're different."

A sharp intake of breath. The shattering of glass on the floor. A cold liquid running down Rory's leg.

E flew out of the booth, glass flying off of her calves. "Rory! What the hell?" She grabbed the hand of her paralyzed friend, dragging her to the bathroom, a place where all secrets were safe.

She finally got a good look at Rory's disheveled appearance. "Okay, I know you pretended the only thing bothering you was my inability to be on time but you'd never leave the house looking like this. Spill. What's going on in Roryland?"

"Nothing."

"So the gossip is true."

Rory went on the defensive, practically yelling at E. "What did Jess tell you?"

"Rory, you were in the bathroom with him. Dean Hessler walked in. Jess didn't have to tell me anything."

"Nothing happened in the bathroom."

"That's not what Dean Hessler told Miss Fairfield."

"Dean Hessler is a California prick who enjoys banging sixteen year olds. You really believe what he says?"

"Are you having problems with Logan?"

"Logan and I are fine."

"If you are with another guy, especially Jess, in the bathroom, I'd say fine isn't what you and Logan are."

"Don't think of this as an opening to get to Logan. He doesn't want you."

"How do you know?"

"Oh my god, don't tell me you actually thought you were going to get him back?"

"I didn't say that. I just don't think you should assume he doesn't want me when you are off blowing Jess."

"You know I don't get on my knees for anyone. That's your job."

"Then was it the other way around?"

"Why does it matter to you?"

"You're the good one Rory! I'm the one who is supposed to be caught in bathrooms with guys like Jess. Not you!"

"What's that supposed to mean? Are you saying I couldn't be with a guy like Jess?"

"Guys like Jess don't want anything to do with you after they get up your skirt."

"Correction; guys don't want anything to do with you after they get up your skirt."

"Are you mad at me or something?"

"Wow, it took you this long to catch on? I gave you too much credit."

"What did I do?"

"What did you do? Did you really think all would be fine? You ruined my life! You slept with my boyfriend! You almost got me kicked out of Chilton! You humiliated me!"

"I thought we could move past that."

"I don't forgive."

"So what, you hate me now? Come on Rory, that's ridiculous. We've been friends since we were five."

"I don't need friends."

"Jess isn't going to be your friend. You might think he cares, but he doesn't. He's great for a week, but all he's only a good fuck."

"Maybe all I want is a good fuck."

"So Jess is a booty call? Rory, you can't do this to Logan!"

"I can do whatever I want to Logan because he's mine. And for the record, Jess isn't a booty call. I wouldn't cheat on my boyfriend with his best friend."

"It was one time. We were drunk. Why can't you get over it?"

"It's more than just Logan."

E looked down at her feet, her front breaking down in the face of losing the only friend she had. "I'm sorry."

Rory's eyes were hollow. She had no feelings left. Well, except one very important feeling. "I hate you."

E was still in denial, still thinking her charm would get her her old life back where everything was about R and E. "We can fix this. I'll stay away from Logan. Or Jess. Whoever you want, I'll stay away from."

"It's too late to make up, sweetie."

"Don't do this, Rory. You don't want to be my enemy."

Rory moved closer, resting her hands on E's shoulders. "Oh, I think I do." She gave E a hard push into the wall, her patented wicked smile planted on her face. "Think of this as war."

She walked away, leaving E to wash the blood out of her blonde hair. "And I don't play nice," she called back, her heels clicking on the tiles as she left E all to her lonesome.

Drawing blood certainly wasn't the normal definition of playing nice.

* * *

E stared into the mirror.

Mirror, mirror, on the wall, who was the scariest bitch of them all?

Place your bets now. And remember, Rory is one crazy bitch. Of course, don't count E out. She did almost get Rory kicked out of Chilton. And you probably want to know how. Soon, all will be revealed. Or at least the parts that Richard and Emily didn't have erased from everyone's memory.

"She doesn't want to mess with me," she said, talking to the mirror. "I know everything."

* * *

Rory stepped out of the bathroom, a little pissed off, a little confused and a lot drunk. She flipped open her compact mirror, frowning at her reflection. She slammed it shut, not liking her look of Catholic school girl hobo.

_Could her hair have looked much worse?_

She felt a pair of eyes on her frame. She knew who it was. No one else violated her regularly like that.

She scanned the room for him. There he was, Jess Mariano, sitting at the bar, sipping on a rum and coke.

She didn't take her eyes off his. You could say they were partaking in one intense round of eye sex. Blue on brown fornicating into one odd color.

He finally broke eye contact, looking down into his glass and shaking his head.

She glided over to the bar, turning so her back was against the bar, her hands pushing her off the wood. The little chest she had was pushed out into his face. "I believe this constitutes as stalking."

Rory's barely A's weren't going to pull his attention away from his rum and coke. That and he didn't want to give her the satisfaction of thinking he enjoyed every inch of her. "I didn't know you were important enough to go incognito."

She realized she had come over to see him in her stained Chilton skirt. Her hair was in a ponytail. Not her finest fashion hour, indeed. "I didn't have time to change."

He shook his head in an indifferent manner. "Okay."

She slumped back against the wood, her chest deflating as soon as she dropped her hands, one left lingering on the bar, her fingers dangling in the air. "Not that I would change. Or wanted to change. If I knew I was going to see you, I definitely wouldn't have taken the time to change."

"You like looking dirty. I'll remember that."

"That's not what I meant. What I meant is that your opinion doesn't matter to me."

"Yes it does."

"No, it doesn't. Not even a little bit. None whatsoever. I don't even think about you when I am getting dressed."

"I'd prefer if you thought about me when you were undressing."

"I think about Logan. Not you. Never you. Not once you." Jess watched her lips. The words that were coming out of them were of no interest to him. He just stared at her pink lips, watching as she rolled her tongue around her mouth, the way she spoke too quickly for her mind to catch up, forcing her to say the same thing over and over.

"You're rambling." Smirking _really_ was his thing.

"No I'm not. I'm talking."

"A lot. You're using different words to say the same thing. It's amusing."

"I'm leaving."

"I didn't invite you over here." He moved his hand on top of hers, making sure their fingers danced with each other just long enough to make Rory shiver. She visibly shook, before jerking her hand away.

"Do I make you shiver?" He asked, in a deep, husky voice that Rory imagined he used when he was about to come. Wait, no she didn't. Rory wouldn't think about that, would she?

She examined her hand, unsure of what had just happened.

It's called electricity, sweetheart. Look it up in the dictionary sometime. It will say "See chemistry." Read that one too.

She exited without saying another word, without giving him another look, without remembering why she even came over there in the first place.

E stood behind the bathroom door, witnessing the entire interaction. She had the ammunition she needed to get started. But first, she needed to go have a bit of fun with Jess.

* * *

E grabbed Jess' drink out of his hands, sucking on the left over ice cubes. The girl seriously needed to go to an AA meeting. "I need you to do me a favor."

He hadn't undressed E with his eyes since she had returned. He looked up and down her body. Not bad. "You haven't let me give you a proper homecoming. I'm offended."

The waiter brought over another rum and coke for him and a Shirley Temple for E. Lorelai must have seen the little alcoholic and decided to play the mom card. "I need you to fuck Rory Gilmore." E took one of the cherries out of her drink, biting the end off in a manner that Nancy Reagan certainly wouldn't approve of.

He choked on his coke and rum, knowing he couldn't have heard what he thought he heard. "Excuse me?"

"I know you want to. She'd be your greatest conquest."

"This is feeling a bit too _Cruel Intentions_ for my taste."

"I didn't say you could put it anywhere.'

"Why do you want me to fuck Gilmore?"

"Because she wants it. And I want you to give it to her."

"I thought you two were bosom buddies. Didn't you make out in Finn's hot tub two summers ago? Girls who make out together stay together."

A heavy sigh was released from her body. Once you crossed E, you were dead to her. "We were friends. That's past tense, in case you didn't notice."

"I'm not the one who was kicked out of boarding school."

"So will you do it?"

"What's in it for me?"

"Besides the obvious?"

"I need a little more incentive than just seeing Gilmore's thong."

"If you do it right you'll see under her thong."

"I don't need sex tips from you."

"I heard you were a bit rusty."

"I had to take a break. I didn't want to be put down like father's race horses in my prime."

She huffed. "What do you want?"

"Take care of Logan."

"Huh?"

"Take Logan out of the picture. Distract him with your fantastic rack. Whatever. But make him disappear."

"I'm not a magician."

Two could play at the manipulation game. "I'm not sure if I should fuck Gilmore. It'd be sad to lose the last standing virgin."

"Why do you want your best friend to vanish from Rory's life?"

"I can't tell you all my secrets," he teased, knowing she wouldn't believe him even if he let her in on his little embarrassment of the moment.

She rolled her eyes. "Fine. I'll do it."

"Please do him, preferably. And tape it."

"What makes you think he'll take the bait? Rory is certain he is in love with her and only her."

"He's a manwhore. He can't say no to free pussy." He paused. "What makes you think Rory will give up her virginity?"

"I just have a hunch."

"A hunch, huh? Care to divulge why you have this hunch?"

"You have your secrets, I have mine." She batted her eyes at him, running her hand across her chest in a way that she knew would have all eyes right on her, even girls admitted, perfect rack.

He smiled. "Fair enough. Do you want to shake on this? Or better yet, let's seal the deal up in my dad's penthouse."

"I think I'll pass. And let's be honest here for a moment. Who do you really want to take up to your penthouse?"

"I prefer the girl to be conscious and willing."

"Are you sure you don't prefer Audrey Hepburn look-a-likes now?"

"Those are hard to come by."

"I happen to know one."

"It's just a game."

"The most dangerous game," she reminded him.

"If you don't bring protection, yes."

She laughed, shaking her head at his evasiveness. "You'll never admit to it, will you?"

"To what?"

"That four letter word that seems to be lacking in your vocabulary. And life."

"Fucking is seven letters. Man, you really are dumb."

"Now I'm definitely not joining you upstairs."

"Oh come on, one last romp before Rory kills you."

E spun around, leaving Jess alone in the bar, without an ass to tap. Must have been a bummer for our very own Casanova.

He watched her leave, noticing the traces of red in her blonde hair. He knew who had done that. It was the same girl that would eventually leave scars on his back.

* * *

The race for Rory's virginity had just heated up. The question was, who would get up Rory's skirt first: Logan or Jess?

One thing was for sure; someone was going to unlock Rory's chastity belt before they all went off to college, which was a relief, because Rory Gilmore did not want to be devirginized in some frat house. Heiresses didn't do it like that.

* * *

**Ending Author's Note**: I'm torn about having Rory and E go at it in a big KY Warming Gel fight, like in _Old School_. The Hartford Boy's Club could coordinate the whole thing and they would fight to the death. It'd be so boss, right? I kid; I'd never go there. I don't want to lose my Feminist Card, even though I've probably lost 1000 feminist points for this story.

Ah, I have written the great puzzle. Is this a game for Jess? Maybe. Is this love? Oh you're hilarious; I'd never give that away (no spoiler alert: the robot falls in love! here). Or will I be going all _Cruel Intentions_? Hopefully not since the banging the virgin just because but falling in love thing is kind of, um, cliche. But I do like the possibilities here. And what is E going to do to Logan? Give him crabs? Crossies that she is that dirty!

**Reviewers**: I put this at the end, but don't worry, it doesn't mean I wasn't thinking about you the whole time: Thanks for the reviews from last chapter! They seriously make me oh so very happy. I love reading your thoughts on me. I wonder why? Self absorbed much? Yes! (I wasn't ambiguous about that question at all).

Yesterday was my birthday, so jump out of a cake in your review for this chapter. And sing some dirty song. Preferably something that involves your milkshake or pimp juice.


	4. I Never

**Chapter 4**: I Never

**Author's Note**: Today, I leave for a week long vacation (aka rehab). I'm going to attach my Mac to my body so I can some get some writing done, but if they do a full cavity search, I might not get a chapter in for two or more weeks. Not that I want to put you through those kind of withdrawals. I understand this story is like heroin and I am enabling you (but I like enabling you and I know going cold turkey is not an option). But if I don't get any writing done while I'm laying by the pool, you can all burn me. I promise!

**Disclaimer**: I made the executive decision after conferring with my Keebler elves and my one stop candy stop that I should probably bump up my story rating to an M. It protects the kids and allows me to talk about tits and mouths and other things that the Parents and Family crazies who rival PETA in scaring me would call "mind blowingly inappropriate." So from now on, anything that disturbs you or violates you, like the licking of lollipops, isn't my fault. It's the dirty in me.

Kinsey owns sex. Well, at least in the psych world. Don't want to offend Jenna Jameson here.

* * *

When E came marching up to Tristan DuGrey in the library he knew he should have run the other way. Whenever she wore her Gucci black leather knee high boots she had her bitch face on and you didn't want to get mixed up in that perfect storm of leather, MAC Cherry ice lip-gloss and blonde hair.

The bitch really was back.

She leaned over his table, making her cleavage visible and certainly not out of reach of his hands.

Every undersexed Chilton boy was leaned back in his chair, blood rushing to the one place in his body that wasn't easy to hide. E's cleavage glowed like God himself had put a holy light around it.

Some guys would say it was just like heaven.

"Hey, Tris," she said, in that deep voice every phone sex operator used. E got it from smoking a pack of French cigarettes every day.

She played with the third button on her crisp, collared shirt, the black lace of her bra becoming increasingly visible.

"Not a fan of the dress code, I see." He forced himself not to look up. Looking up in the past had ended in either a cold shower, being left naked in the janitor's closet, alone, or worst of all, forcing him to say yes to whatever she asked.

"You know what's great about buttons? They easily come undone." She popped another button with her finger, the valley between her breasts hanging out for any of these geeks to jerk off to under the table.

Just don't get any on the books, boys. Those stains never come out.

"No," he said coldly.

"I haven't asked you anything, Tris."

"Stop calling me that."

"Would you prefer if I purred your name in your ear?"

"I'm not taking part in one of your little games. I can't go to jail again. They'll kick me out of this place."

"But bad boys have to be punished."

"Shut up, E. Your act doesn't work on me anymore. I am immune."

"Aw, did Rory make you fear tits? You're like one of those sad animals that are released into the wild and don't know what to do."

"My hands don't want anything to do with your tits."

"What about your mouth?"

Tristan slammed his book shut, making E move a step away from him. Tristan was known to have a bit of a temper. "Why are you in here? Shouldn't you be off getting fucked by Mariano or Huntz?"

"See, it's the talking to you that will eventually lead to the fucking Huntz."

"Mariano figured out your vagina would rot his dick off? I'm impressed."

"So that's where yours went."

Actually, Rory kept his in a jar. Don't cross Miss Gilmore; she'll castrate you.

"I can't believe they haven't closed down your gateway to hell yet. Someone needs to call the EPA and tell them about the toxic things you're holding between your legs."

She took a step in his direction, grinding her stiletto into his foot. He probably mumbled bitch or another insult that would make our mother's blush, but who didn't know E was a bitch? Her parents didn't ship her away because she was a delightful Georgia peach.

Think Regina George but brilliant.

"Listen, Tris, I just need you to give me something."

"I'm not getting caught up in whatever you are plotting," he choked out, trying not to cry like a pussy from the pain she was inflicting on his foot. E would squeal with delight if she made him cry.

She pressed her stiletto down harder, grinding back and forth. "You feel that? That's just a little pain. And it'll eventually go away. But if you don't do what I want, I'll be forced to make your entire life feel like this. Nonstop. And I don't want to do that. I'm a good girl, but people just do things that force me to be bad."

"If I agree to help you, will you remove your heel?"

"Of course I will. I'm not crazy."

"Enjoying torture isn't insane at all," he deadpanned, searching for feeling in his foot that Gucci had destroyed. "What do you want?"

"Rory's panties."

"I have no clue what you're talking back."

"Tris, my heel, in your foot, everyday. Metaphorically speaking, of course. I can't wear the same shoes everyday."

"Why would I still have Rory's panties?'

"Because you're obsessed with her in an illegal sort of way."

"And why do you want her panties?"

"I forgot mine today." Add a unicorn, a gun and cinnamon bun hair and this was every boy's fantasy that was in the library at the moment. It was even better than their virtual Laura Croft.

Tristan reached for her wrist, applying just enough pressure to scare her. "I don't want to hurt you either, darling. But I'm also not in the mood for your games."

"Does it make you feel like you're still a man grabbing me like this?"

"Why, is it turning you on?"

"If it was turning me on you wouldn't be wearing any pants."

"Still the little slut, I see."

E's normally sparkling blue eyes had gone cold. "I'm not a slut."

He squeezed harder, her wrist almost purple. "Aw, did I hit a nerve?"

"Give me the underwear DuGrey. Unless you're wearing them right now." She wiggled out of his grip, knowing she had won. Being a drag queen wasn't popular at Chilton.

"Shut up."

"If you just hand over Rory's underwear, I'll leave you alone."

"Fine," he said like a four year old who had just been sent to the time out chair and had his favorite toy taken away. And he kind of had. He _loved_ Rory's panties.

"Oh I forgot to ask, are they clean?"

"I didn't steal her dirty underwear."

"No, I mean how many times did you whack off into them? Semen underwear is of no use to me."

"They're clean."

"Did Francesca use bleach?" Yes, the virgin wore white underwear. Could she be more obvious?

"Yes."

"What an angel. Thank her for me. Of course, you probably do that everyday when mommy and daddy are away."

He pulled the underwear out of his pocket.

Interesting hiding place, Tristan. Planning on a panty love fest during lunch? Say high to Huntz in the bathroom for us. "Now go. And button up your shirt. No one needs to see that."

"I can't figure you out DuGrey."

"What's that supposed to mean?"

She simply smiled, another button popping open. It was a good thing nuns didn't teach at this school. "Have a good day, Tris. And I'll try to get these back to you, but I can't make any promises."

* * *

Was E auditioning for the Chilton production of _Basic Instinct_? Everyone was fine with the possibility that she might ice pick them to death if she ever ran out of strawberry gum, but the unladylike manner in which she was sitting in the Headmaster's office was a bit much.

Emily Gilmore would have glued her knees shut to teach her a lesson.

At least she had opted to not walk into her meeting with Charleston in that black lace bra. The man was not a spring chicken. Heart attacks happened. No need for E to get that special feeling of killing a man with your cleavage. That was a feeling only nice girls should experience.

The wait was the worst part for her. She had psyched herself up for this. Wiped off her lip-gloss. Practiced a range of devastated expressions in front of the mirror.

Charleston needed to get his ass in his office pronto before she had a divalike meltdown and started stripping in front of Miss Higgins.

Remember Mariah Carey during TRL? E used to have those meltdowns on a daily basis before she went off and became a little reformed Goldilocks.

Waiting made her do things, like blow off of some girl's stomach. A good girl she was not. Until right now. Right now she was an angel in Italian leather.

Charleston fumbled with the doorknob, almost falling into this office. He had sprinted the whole way, knowing he couldn't leave Miss Rigby waiting.

Sweat was pouring off his face. Ew.

"Sorry to keep you waiting, Mss Rigby. And welcome back to Chilton. Settling back in well, I hope." As he fell into his chair, his ten chins jiggled around, sweat continuing to pour off his face. E had to force the vomit back down at the sight of Jabba the Hut dying right in front of her eyes. When he licked his lips, she almost lost the muffin she had consumed that morning.

Which actually wouldn't be that bad. She hadn't found time to make it to the bathroom yet today to get rid of the blueberry muffin that would go straight to her ass, so why not double task?

Bulimia and scheming. The perfect breakfast.

She forced an expression on her face that resembled a smile. "Well, I miss mommy and daddy terribly, but I am so happy to be back at Chilton. My education has always been my top priority and those French boarding schools are just one nonstop party. No one wears clothes! It wasn't a conducive environment."

He inwardly cursed his appearance. Just because he was seventy didn't mean he was blind. He took Viagra. He had hair plugs. He longed to still impress the ladies, even his students, especially the ones who didn't cross their legs. "You were always so gifted. It was such a shame that the Hartford lifestyle misguided you for awhile."

Um, no. Thank God the Hartford lifestyle misguided her. Who else would we get coke from? An actual drug dealer? So not happening!

She looked down at her feet, then up, giving him that kicked puppy face she did so well. "Yes, it appears someone else at Chilton may be lost. That's what I'm here for, actually. I couldn't let another Chilton girl, especially my best friend, lose her way."

_Best fucking friends forever, even if they were ripping out each other's hair, right? _

"This meeting is about Miss Gilmore?"

E blinked a few times, forcing tears to form in the corners of her eyes. Girls fake everything. "I'm afraid so. I found these in the library." She held up a pair of white La Perla underwear.

Good intentions were best left for people who worked at the Red Cross. And the pope.

Charleston knew that girls these days had an aversion to wearing underwear. He'd put a paragraph in the dress code that specifically required the wearing of underwear everyday. Had Rory lost hers? "I'm afraid I don't understand."

"I found Rory's underwear inside of _Anna Karenina_." Violating a classic? To believe this, you would have to believe Rory Gilmore had an evil twin. Rory would never have sex in front of the innocent books!

"How can you be sure they are Miss Gilmore's?"

E pointed out the little monogrammed RG on the left hip. "Rory has all of her underwear shipped in from France. And on each pair, she gets RG monogrammed. RG is Rory Gilmore."

"Why would Miss Gilmore use her underwear as a bookmark?"

"Oh you didn't hear? Rory was caught in an unsettling situation with several Chilton boys last week at her mother's party. It appears she is a sex fiend!"

And a witch! Burn her! Burn her!

Charleston shifted in his chair, not liking where this conversation was headed. "Miss Gilmore is one of our most promising students. She is focused, hardworking, has perfect attendance. Those aren't the type of girls who fornicate with a male peer in the library."

"I wish this wasn't true. She's my best friend, Headmaster. I hate to see her this way. That's why I came to you for help. She wants to go to Harvard. If she continues with this behavior, she'll be in a nunnery having Jess Mariano's child! We can't have that. And she loves books. To violate a book with her dirty underwear means something is wrong. A call to her mother and the elder Gilmore's should be made."

"I'm not sure I can do that from just a pair of panties."

Tears fell from E's eyes. "Do you not care about your students? I thought this was an institution that molded young minds and guided them! If one of your minds is lost, you must help it become found again. If you ignore this you will find underwear in your office one day!"

She produced a few sniffles that would have made even Hitler want to comfort her.

Charleston reminded her of why she was sent away to boarding school. "Fornication on school property is a suspendable offense."

"Sometimes the toughest lessons come with the toughest consequences. Do what needs to be done. My friend is drowning in sex!" Give the girl a hanky and an Oscar.

And a rubber room at the Hartford insane asylum.

Or maybe what she really needed was protective custody when Rory put this together 6.5 seconds after Charleston showed her the panties.

E handed Charleston the panties on her way out. Now there was an image we never needed: Charleston touching Rory's La Perla underwear.

First Tristan's love stains, now Charleston's hands. And it will only get worse when Richard and Emily Gilmore are brought in on this job.

Watson and Sherlock will surely pull out their magnifying glasses to examine the panties in question.

Her panties will be more infamous than Monica Lewinsky's semen-stained blue dress.

"Miss Rigby," Charleston called after her. She spun around, in that perfect shampoo commercial sort of way.

"Yes?" she asked sweetly, her face the perfect picture of slutty innocence.

"We pride Chilton in sending well bred men and women out into the world. Please try to keep your legs crossed." He might have liked the view, but he couldn't encourage it. He didn't need an outbreak of syphilis on his hands again.

"Sorry, sir. I developed a terrible rash from the tights and haven't been able to cross my legs all day. As you can guess, the boys have been terribly rude."

She really was a master bullshitter. Rory would almost be in awe of her if she didn't hate her so much.

* * *

Rory was never a fan of public displays of affection. It was like being forced to watch porn a 13-year-old had shot with his camera phone. It was raw, unpleasant, always in bad lighting and never involved people she wanted to spend more than two seconds thinking about, much less see grope each other in a sea of plaid and hair gel.

Nothing was ever edited out. The moves were messy. There was no build up. One minute there was plaid; the next minute there were boobs. It was only pleasing for the male part of the encounter.

And for Alex Ostrof, because she was a big tited "foreign exchange" student that Rory was sure was a prostitute when she lived in France. At least, that's what she wrote on her blog, so it must be true.

Alex Ostrof. Rory had always been tempted to shove a stiletto into her jugular. Her fake French accent and insistence on not wearing a bra gave her automatic slut status in Rory's mind and since E, Rory had very little patience for sluts.

Alex wasn't helping her case at this very moment by sucking face with Jess Mariano right behind Rory.

The smacking would not stop. It was set on replay in Rory's mind, the cd never moving on to the next song.

Normally, this wouldn't bother Rory. She'd be too busy mentally writing the story of how and when she'd lose her virginity. But today, she wanted to strangle Alex. Or at least cut her tongue out with kid safety scissors so Jess would have no use for her (and it would be incredibly painful, which is what that French prostitute deserved).

S_low down there tiger! At least offer Tits McGee a Valium before taking away the holy grail of Chilton tongues. _

Rory's hand shot into the air in a frantic pursuit for Mademoiselle Coco to put a cease and desist order on this herpes fest.

Mademoiselle Coco was always a bit snookered. It didn't matter if it was nine in the morning; she had the faint smell of vodka and tomato juice on her breath. And since she didn't believe in bathing more than once a month, the air around her was always thick with the smell of sweat, Yves Saint Laurent perfume and smoke.

She was attractive in a Kate Moss sort of way and if she would have taken the occasional bath, she might have gotten the opportunity to blow Jess Mariano.

_What a lucky girl she would have been! _

But the problem with Mademoiselle Coco's drunken state was that she didn't pay much attention to her class, too busy flipping through Vogue and cursing in French about how fat her thighs were. And when you interrupted her pre-hangover exuberance, she would puff smoke in your face and call you a stupid little cunt.

But because she said it in French, you had to smile. It sounded lovely.

"Oui, Mademoiselle Gilmore?"

"Chilton is an institution for learning, is it not?"

"Rory, I will not answer you if you do not ask the question in French. This is French class, is it not?"

"But we don't know how to say what I need to say in French," Rory whined. She only knew how to tell people she was bleeding from the head. And that zombies were attacking.

There was this freak in her class named Dean or Bleam or something like that who was obsessed with zombies, so the only sentences the class were taught had to do with death and zombies because Mademoiselle Coco had a crush on the floppy haired psychopath.

"Then it must not be important, non?" But zombies were certainly important!

"So Alex and Jess are allowed to swap fluids while I am trying to conjugate verbs because they are French kissing?"

"French is the language of love, oui?"

"So if I started having sex with someone on my desk right now it would be fine because French is the language of love?"

"It would depend on if you were speaking French throughout the encounter."

Rory had to grab the sides of her desk to keep herself from beating Mademoiselle Coco to death with her French book. The thing weighed like five hundred pounds, so it wouldn't take long to give her a little blunt force trauma to the head. "Are you serious?"

"Paris is the most wonderful city to fall in love. Persian men understand how to make the woman happy." So did Jess Mariano. That or Alex had a disorder where she moaned a lot.

_Over-exaggerated porn star moan, party of one!_

"I can't believe you are letting them continue!"

Jess pushed Alex Ostrof's tongue out of his mouth, sick of the taste of powdered doughnuts. He looked at her, her eyes still closed, staring dreamily in his direction. She probably expected him to lean his forehead against hers, still panting, and whisper perfect nothings, brushing his nose against hers.

Maybe if she wasn't such a slut he might do that.

Instead he leaned forward, edging himself closer to Rory, and ran his hand down her neck.

She instinctively smacked his hand away, not wanting the feeling of his smoldering heat on her cool skin. "Don't touch me with that hand. We all know where it was right before class."

"Sorry, I can't help myself. You have a lovely neck."

"How about you go back to swapping diseases with the French prostitute back there and leave my neck alone?" If he didn't, she was going to have to scrub it for at least an hour with bleach. The stench of slut didn't wash out easily.

He shook his head, like he could read her mind. "I don't think that's what you want."

"You're right; I wish you'd walk in front of a bus." At least she didn't want to push him in front of a bus. Small victories!

"I'm not into murder-suicides, Freckles. We aren't star crossed lovers."

"Why won't you leave me alone?" she almost begged.

"Because nothing makes my day more than watching your cheeks flush."

Mademoiselle Coco interrupted their little Hepburn/Grant moment. "Rory, the Headmaster wants to see you."

"You already lit E on fire? I'm impressed, really." Jess did have a thing for the psycho bitches. They gave it way better than they got it.

She smiled that dopey smile she always smiled at him when she was trying hard not to flirt. "You know I'm into slow torture."

"Ah yes, the stapler through the penis."

"A slow, sweet torture," she said in a eerily low, husky voice.

"Charleston's office after sixth period?"

"Take off your pants, put them outside the door and maybe I'll show up."

"And if you don't?"

"You and your hand will have one sadistic party together." Unless he decided to go find Finn or Colin or both in the shower to work out all that sexual tension.

"I hear my hand is warmer than you." It depended on which part of her you were referring to. Certain parts of her were pulsating at this very moment.

"Once a frigid bitch, always a frigid bitch."

"Is that what they told you at the convent?"

"Actually showed me. They all have it tattooed on their asses. Want to see?"

"I can't look at one of God's asses. It would be wrong. Immoral."

"And you're such a morally upstanding boy."

Mademoiselle Coco hadn't had nearly enough vodka to listen to all this verbal copulating. "Miss Gilmore, the Headmaster is waiting! You can flirt with Jess later."

Rory's face broke. "I don't flirt with people who give it to any girl who knows how to lie still on her back."

"Or situate herself upright," he added, reminding Rory that he did it, a lot.

Alex, in her horrible fake French accent, decided to use her words instead of her tongue for the first time in her life. "Rory, Jess iz boutiful. You can take him. My pussy iz tired."

"Oh my god, you're from Connecticut! You lived in France for like a year! Speak proper English. Even Mademoiselle Coco manages to form proper sentences! It's not that hard."

"Iz you jealous of moi?"

"Of your perpetual case of syphilis? Or of the fact that every boy in this school has given you a pelvic exam?"

"You iz such a bitch. No wonder Logan iz fucking everyone but tu."

"Quit substituting easy words with French. You make no sense!"

Paris interjected in her perfect Gellar way. "Rory, Jess isn't worth throwing down with Miss Les Miserables back there."

"This isn't about Jess! This is about the fact that people can practically fornicate in French class because Mademoiselle Coco is too full of vodka to care and that certain people walk around this school saying iz this and iz that and it's okay just because they never learned how to cross their legs."

"Rory, Headmaster Charleston, now!" Mademoiselle Coco was going to pull out her paddle if Rory didn't exit, stage right, soon.

"Iz going!" She stalked out of the classroom, slamming the door behind her, pressing her heels so hard against the wood floors that a trail of smoke was following her.

That was how high society girl scouts started fires. All you needed was a pair of Manolos and anger seeping out of your veins.

* * *

Miss Higgins was wearing a lavender angora sweater that was probably sewn by ten little Asian children in a sweatshop and a visually paralyzing brooch. Rory had to shield her eyes from the atrocious mismatch to keep herself from tumbling to the ground in an all encompassing fit of laughter.

Her grandmother had sent her to princess classes when she was five, so she knew how to be politefully bitchy. "Lovely sweater, Miss Higgins. Donna Karen?"

"Walmart," the forty-five year old virgin blushed. Like every other person at this school, she feared the critical eye and venom-laced tongue of Miss Gilmore. The only person in Hartford more terrifying was Emily Gilmore.

Rory wrinkled her nose. Fried chicken hands had probably raped that sweater in the dressing room. "That's tragic. Oh well. Someone has to buy Juicy knock off sweat pants." She tapped her freshly manicured fingers on the desk. For some reason, she'd decided on the color black this week. Was black the new French manicure? Or just an awful trend we have Avril Lavigne to thank for?

There was so much to blame Canadians for. Celine Dion. Flannel. Maple leaves. And that stupid Britney Spears version of a punk.

Joe Strummer's guitar gently wept for sure.

"So is the Headmaster waiting for me?"

Miss Higgins, who rarely looked Rory in the eye, had a look of wicked pleasure on her face. Rory instantly recognized that look. It was reflected back to her every morning when she applied her Chanel Inimitable mascara. "Oh, he's most certainly ready for you." She looked down at Rory's bottom, making those lady leaning tendencies seem more like the truth and less like a vicious rumor Rory decided to make up because of Miss Higgins love for Puma sweat pants.

Only stoners or lesbians wore those.

"Has it been an unusually cold day for you, Miss Gilmore?"

"Excuse me?"

"Nothing. Don't want to keep the Headmaster waiting. He might get his panties in a bunch."

And everyone thought Rory and E were the only ones who enjoyed sushi at Chilton.

* * *

Instantly, like she had radar for her lost pair of La Perla panties, Rory's eyes noticed the clumped up heap of white situated on Charleston's desk.

Her Snow White face lost any bit of the rosy color it normally held for just a moment as her stomach collided with her ass.

She looked up, giving Charleston her famous "Fuck off and die" smile.

"Rory, please take a seat. We have much to discuss."

Like why her panties were occupying a spot on his desk.

Her mind made a list of all the people she needed to kill: Tristan, for giving Jess the underwear. Jess, for covering them with love stains. And Jess again, for leaving them behind in the boy's bathroom for anyone to find, like E.

And then E, for stealing her Gucci boots when they were thirteen, her favorite pair of La Perla panties and for telling Charleston she was a panty losing slut.

He looked grim, like he was about to tell her that her Diane Von Furstenberg wrap dress was so not in style anymore. "Rory, I have some unsettling news for you."

"What?" she asked, all Bambi eyed, like she'd never take off her underwear.

"Someone found a pair of your underwear in the library."

She eyed the pair of La Perla underwear. They were certainly hers. But she'd never admit defeat. E would not sink her battleship. "Those aren't mine."

"Are you sure? And do remember, we have an honor code at Chilton."

"I'm the president of the senior class, Headmaster. I would never leave my panties in the library." She was also a virgin. That reason would suffice as well.

"They were found in _Anna Karenina_. No one has ever checked out that book but you and Mr. Mariano."

"Then maybe they are Jess' underwear."

"Humor won't fix this situation, Miss Gilmore."

"I'm sorry I couldn't be of more help, Headmaster, but I am not the kind of girl that takes off her underwear at school. Maybe you should check with Miss Rigby."

"She was the one who reported the underwear, actually. Do you think Miss Rigby would report herself?"

"It depends on how sober she was." Oh come on Rory. Everyone knew E did her best scheming when she was under the influence of something.

"She seemed quite sober to me." Charleston wasn't the best judge of this seeing as his eyes were in her crotch for ninety-percent of the conversation.

"She hides her inebriated state well. She's had great practice."

"I have been assured that Miss Rigby has reformed herself. She is not the girl she left Chilton as."

"She still wears Diorshow mascara."

"Is that supposed to mean something?"

"A tiger doesn't change its stripes unless they go out of style. I am an avid reader of Vogue. E's ways are still very much in style. All she needs is a girl on her arm and she'll be a walking icon in plaid."

If only you two would kiss and make up you could be that girl on her arm, Rory! Leave all the boys behind! Thelma and Louise ended so wonderfully, right? Right? RIGHT?

Charleston was tired of Miss Gilmore trying to talk her way out of Pantygate. Time to pull out the truly incriminating evidence. "Miss Rigby's initials are ER, are they not?"

"I suppose, unless she got a name change after all that electroshock therapy."

"Well these panties have RG monogrammed on the hip. Any guesses on what that stands for?"

"Ready, set, go?"

"There is no S in the monogram."

"Maybe she forgot the S. She isn't that smart."

"I've been informed about your new extracurricular activities," he blurted out. He wasn't going to go down without getting in a few punches on this Raging Bull.

"Outside of serving as senior class president, head social chair, playing tennis and being perfect?"

"Miss Gilmore, the truth is the pillar on which we all stand on. At least have enough respect for yourself to tell the truth."

"Hypothetically speaking, so what if those are my panties? You can't suspend me for leaving my panties in _Anna Karenina_."

"Tolstoy would not…"

She attacked, knowing she was smarter at this point in her life than he ever would be. "How do you know how Tolstoy would feel? Have you ever read _Anna Karenina_? Or _War and Peace_?"

"So you are admitting those are your panties?"

"No, I said hypothetically."

"Fornicating on school property is a suspendable offense."

"You can't prove fornication went on in that library."

"I have eye witnesses that place you and Jess Mariano at the scene of the crime." Who had E paid off? They wouldn't be alive tomorrow if Rory found out who this supposed witness was.

"The crime? Forgetting your panties is not a crime." Unless your vagina looked like Britney Spears or you had recently given birth. Then it was a crime against humanity.

"What would your mother have to say about this?" He _really_ didn't want to bring in Chilton's most famous slut on this case.

"Call her and find out. She loves getting calls from idiots. She thinks they're fun. Much more entertaining than those Botox injected hags she's forced to have lunch with everyday."

"Then what about Richard and Emily? They are paying for your education, if I remember correctly."

"I'm the golden orb of life in which they rest all their hopes and dreams on. Your word against mine won't mean much to them. My grandfather might even have you fired. And he'll own this place. How do you feel about magenta curtains?"

He tried to speak, but she cut him off. "Oh who cares what you think. You're a man. You're only necessary for one thing and I don't need impregnating anytime soon. Besides, if I was looking for a donor, there is much prettier specimen floating around in Hartford."

"Then Harvard! Harvard certainly won't accept someone who was suspended for fornicating on school property, especially if I add that you have developed an addiction to Oxycontin."

"I might be scared if I wasn't sure you were bluffing. I am well on my way to being Valedictorian. I scored 2300 on my practice SAT's. I highly doubt Harvard will even glance at your letter of recommendation."

"Oh they most certainly will. I've kept many students from going to Ivy League schools. How do you feel about NYU?"

"Charleston, sorry to break it to you, but your threats don't scare me. I'm a seventeen-year-old girl who was raised in high society, attends private school and deals with the likes of Miss Rigby. People like you, who are so easily manipulated by boobs and blonde hair, can't do much to people like me."

His head was spinning around like one those charming cartoon characters. "You're getting a weeks detention for this little stunt."

"Don't tease me," she laughed, because she had won, even if she was going to be punished.

"And I am making phone calls to your mother and grandparents."

"I hope Richard invites you to the club. I'd love to see what he does with a nine iron."

"You're dismissed," he looked down at his desk, "and take your underwear with you."

"Where is detention held?"

"Miss Higgins will write you a slip."

"Is this going on my permanent record?"

"Of course it is."

"Thank god for erasable pens and white out."

"Enjoy spending a week with Dean Hessler."

"And you have fun making that call to Harvard. I wonder how you'll explain why you have a Dean on staff that sleeps with his students? That'll be a tough one to spin."

"You wouldn't…"

"I have a meeting with Harvard next week. Our chat will be fascinating, I'm sure. I'll be sure to put in a good word for you," she winked at him, and then left his office, a thousand thoughts pulsating through her mind.

But the one that required the most attention, that was glowing like the neon motel signs on the highway, was the most obvious one: Miss Rigby must die.

* * *

Rory was always warned not to become like her mother. Her mother was the girl who left her panties in the torn pages of a Tolstoy book; the girl who spent every afternoon in detention until she realized windows opened from the inside; the girl who was caught in the janitor's closet without a vital piece of her Chilton uniform on; the girl who got pregnant at sixteen.

Trouble wasn't something Rory Gilmore had even experienced until E decided to lose her mind and forget sobriety was necessary some of the time to function, so room 306 wasn't a place Rory had spent much time.

She didn't have her name engraved into any of the desks or nail polish stains left on one of the chairs.

Being alone in that room was almost suffocating for Chilton's Princess. Her mind wandered to places where the next day, Charleston found her body chopped up in perfect little pieces in the closet, all the blood drained and another pair of La Perla underwear stolen off her body.

_Someone had watched a bit too much Dexter. _

She heard footsteps enter the room.

Hopefully, it wasn't her murderer.

Not the sound of heels, so unless it was one of those woefully unfashionable girls, it must be Dean Hessler.

"Fancy seeing you here, Gilmore," Jess said in a tone that was supposed to covey surprise.

She spun around. This boy followed her everywhere. "You have detention?'

"Until I die or graduate."

"And you actually come?"

"It's a good place to read. No one bothers me."

"You're always alone?"

"It's common knowledge Dean Hessler never makes an appearance. You're such a virgin, sweetheart."

She stood up, not wanting to stay in this terribly lit room a second longer. They could at least buy a nice pair of curtains. "So we can just leave?"

"Or you could stay," he suggested, moving so close to her that he almost stepped on her toes. For some reason, she wore sandals today.

Sandals versus Gucci. No wonder she had lost.

She fell back into her chair to keep his hands from roaming her body. Being in a room alone with Jess wasn't good for her reputation because she tended to do this. Stupid things. Things Audrey Hepburn would frown out and then run Rory over with her moped for.

"Why would I stay?" Yes Jess, why should Rory subject herself to your charm?

"I get lonely in here all on my lonesome sometimes." He almost looked sad. What did Jess have to be sad about? Was he low on hair gel?

"Then invite Alex to come visit you in your fortress of solitude."

"Alex isn't as much fun as you are."

See girls, playing hard to get is much more attractive than shoving your tongue down your crushes throat or getting on your knees in his bedroom. You get your skirt cleaned if you play hard to get!

"What are you reading?" With a question like that, maybe she had decided to stay.

He pulled the book out of his back pocket, letting her examine the cover. "_Killing Johnny Fry_."

"Figures," she huffed. Maybe she was huffing because he pulled the book out of his back pocket instead of letting her stare at his ass, pretending it was all for the sake of literature. What girl wouldn't huff if she lost Jess ass staring time?

He was a little confused. He thought if there were pages and words, Rory became a drooling vegetable. "What?"

"It's porn disguised as literature."

"I know you don't partake in sex but you can't sit here and tell me you don't read about it."

"I didn't say I haven't read the book. I just said figures."

"I read about more than sex."

"Yes, sex and Hemingway. You're such a diverse man."

"I prefer being known as a man of many talents."

"What are your talents, besides the obvious?" Did it really matter what else he could do? His dick giving abilities satisfied most of the female population.

"So you have read the bathroom walls."

"Your handwriting is lovely, by the way."

"How do you know what my handwriting looks like?"

"You've vandalized most of the books in the library."

His lips produced that smile that always got him what he wanted. "Hey Gilmore, want to play a game?" Weren't they a little old for hide and seek? Unless they added a few obstacles, like no clothes.

"I'm not playing doctor with you. You never keep it professional." Come on Rory, let Jess give you a check up. You're looking a bit pale.

"We were six and I was curious. Can you blame a boy?"

"My mother certainly did."

Lorelai had walked in on Jess and Rory showing each other what made them different.

Jess wasn't allowed to come over again until Rory was ten and realized Jess was a little Warren Beatty in the making.

"Well, she couldn't have her princess letting boys in the castle just yet."

"Fantastic metaphor." She played with the hem on her cardigan, not wanting to talk about who guarded her castle. "So where is Dean Hessler?"

"With Gellar in his office." Chilton really did _care_ about its students.

"No way!" She actually had respected Gelllar, before she knew she was giving it to the L.L Bean pants wearing loser.

"Aren't you the gossip queen? How did you not know this?"

"I knew Gellar was seeing an older guy but I didn't know it was Hessler."

"He's why she is less frightening lately. He fucked the uptightness right out of her." That must have taken a lot of thrusting. That stick had been shoved up her ass for quite a long time.

"I can't believe she fell for Hessler. He's been with almost every girl at this school, except for me, of course."

"He wishes it was you in his office instead of Gellar."

"Shut up."

"He could not take his eyes off your perfect ass when you were leaving the bathroom the other day. Not that I blame him."

She stood up, not wanting to listen to Jess compare her ass to peaches or apples or some other food. Baby didn't want to hear that she had back. "I'm leaving."

Jess pulled out everyone's favorite lubrication. "Want a drink?"

She stopped, staring at her favorite bedtime story. "You brought a bottle of Bacardi to detention?"

"I'm a bad boy."

She reached for the bottle, but he pulled it back. "Come on Jess, don't be a Bacardi tease. I've had a long day."

"Without underwear, I hear."

"I'm wearing underwear."

"That's a shame. But it's more fun taking them off anyways."

"Jess, give me the bottle." Alcohol wasn't the answer, Rory. They say don't drink and bone for a reason. Or was it don't drink and drive? Oh well, Bacardi can only lead to boning.

"I'll give you a sip, if you stay and play a game with me."

"What game?"

"'I Never'."

"Why do you want to play 'I Never'?"

"Because getting you smashed is more fun than Cordell's twisted sexual adventures."

She didn't look impressed. "I'm flattered."

"Come on. It'll last five minutes, tops. What better can you do in five minutes?"

Get to third base. Eat a pint of Rocky Road. Make a baby (not that she wanted to get fat, but 'I Never' was seriously lame).

"Fine. But no stupid things to get me drunk like 'I Never kissed a man'."

"But that'd be a lie." So the rumors were true. Jess and Finn did cuddle that day behind the trashcans. And obviously not just for warmth.

"Now I'm intrigued."

He sat down at the closest desk, knowing that if the game went how he had planned, he'd be too sloshed to stand. "Any more rules, Princess?"

"Don't call me Princess." She reached out for the bottle, again, jerking it out of his hands. "So tell me, how soft are Finn's lips?"

"Only if you tell me about all that time you spent in Finn's hot tub two years ago."

"I know you were watching."

"But I want to hear your lovely voice narrate it."

"There are services that do that for only 25 cents a minute."

"How would you know that?"

Because phone sex isn't technically sex, Mr. Mariano. She was still a Virgin Mary in the eyes of God and her gynecologist no matter how many quarters she burned on that hotline.

He smirked at her inability to form a response, her tongue too heavy with embarrassment. It was a rare occasion to witness.

But Jess planned on witnessing a few other rare occasions for Rory, so for him, this wouldn't be so rare. He loosened the tie around his neck, knowing this wouldn't be five minutes tops.

Gilmore's were known to hang from chandeliers singing 'Creep' in a terrible fashion once you got a little Bacardi in them.

"I never called a phone sex line." He didn't need to. He could get any girl at Chilton to do whatever he wanted. One of his regulars would dress up like Princess Leia, but made sounds like Chewbacca when she came, per his request. All he needed was in his little black sex book.

Rory took a swig of the rum, enjoying the sweet taste it left on her lips. "I get bored easily."

"You can always call me." He'd even drop the Chewbacca wailer for Miss Gilmore.

"I don't need you as a friend."

"Well, you've got a friend in me if you ever want one."

"I never liked that song." Jess smiled and took the bottle from Rory's hands, taking a sip of the Bacardi.

"I never pictured you as a Carole King fan."

"Now you're just abusing the phrase 'I Never.'"

"I'm sorry." She got that look on her face, the look of pure mischief crossed with elation. It was probably how she would look right at the point of orgasm. "I never had a threesome."

"Do I have to drink for every threesome?"

She had to take a seat at this point in the game. Her virgin mind couldn't process more than one threesome. "How many have you had?"

"I don't keep count. That'd be demeaning to the girls."

"Not that threesomes are demeaning at all."

"I'm quite good at sharing."

"Just drink up, sailor."

He chugged for a minute, his mind racing to think of something that would royally piss her off. "I never pretended I didn't like Hemingway just because I wanted someone, who might be in this room, to pay more attention to me."

"I hate Hemingway."

"Then you might not want to leave notes in 'The Sun Also Rises.'"

"How do you know what my handwriting looks like?"

"Well, since I'm your stalker, I really don't have to explain myself, now do I? Drink up, Freckles."

"Why would I drink?"

"Because you can't lie in 'I Never.' God is watching."

She didn't want to give him that satisfaction (or any satisfaction for that matter) but if God was watching, the angel certainly couldn't lie.

_Oh as if God had anything to do with it. _

She pushed back, harder. Faster. Stronger. "I never made out with some French slut just because I knew it would bother the girl sitting in front of me."

"Are you sure? I heard you and E used to have some wild times." Making our with your best friend is normal, gosh!

"I never acted like a jerk around everyone but me."

"That sentence doesn't quite work."

"You know what I mean."

"You sure do think highly of yourself." He took a sip. It was time for the game to get a little rough. "I've never been in love."

She rolled her eyes at his admission. "Shocker."

When she didn't take a sip, he couldn't help but smile. "Why aren't you drinking?"

"Why do you think?"

"For some reason, I don't believe that. And what would Logan have to say?"

"I don't know. How about you extract Louise from his face and ask him?"

"I'm sure she's not on his face by now."

She studied her hands, begging her eyes to not let the tears fall that were threatening. She couldn't cry in front of him.

Clenching her jaw, she was bitter. Pissed off. Angry that he was right. "I never cared about you."

She looked up at him, waiting, the corners of her eyes gleaming with tears.

He grabbed the Bacardi off the table, and took a sip.

"Why are you drinking?" When he didn't say anything, giving her that look like she should know perfectly well why he was drinking, she grabbed the bottle out of his hands and took a sip.

Finally, he answered her. "This is 'I Never'."

"Yeah?"

"If I didn't drink, it'd be a lie," he reminded her, except this time, there was nothing resembling feeling in his tone.

Once you let your walls down, it was hard to recover, without a lot of coke.

"Oh." It had hit her. The reason he wanted her to stay. The reason he followed her into the bathroom. It all her hit at this very moment.

"Don't look so shocked, Freckles. But why did you drink? I'm pretty sure you read the obituaries everyday hoping to see my name. And then you cross your fingers hoping, wishing, praying that I suffered."

"I drank, didn't I?"

"That's all you have to say?"

"What do you want? Some grand admission that I care about you?"

"I'd take a Hallmark card. Or you on your knees." Jess really was the king of ruining a moment.

"Can I take that sip back?"

"There are no take backs in 'I Never'."

"Who made you king of 'I Never'?"

He held the bottle of Bacardi in his hands, the tool he used to get her to stay now a nuisance standing in the way of what he wanted to do next. "So how much do you care about me?"

"I might push you out of the way if a bus was headed toward us." She stopped, wanting him to be serious for once in his life. "How much do you care about me?"

He smirked, thinking of the implications of that question. "Do you want me to show you?"

"You can keep your boom box to yourself."

_So that was what Jess called his Johnson._

"I prefer showing people I care in other ways." He reached for her hands but she jerked them back, hiding them behind her back. "Why won't you let me touch you?" He knew why she didn't want his hands on her but fretting her was too much fun to stop now.

"I said I cared about you in a I don't want you to die way."

"And I want to show you how I care about you."

"I'll pass."

"Or maybe you're afraid of what's going to happen when I touch you."

He leaned in, brushing his lips against her cheek. "Like this," he whispered.

He pulled back, wanting her to make the next move. He wanted her on top of him. He wanted her to beg him to be inside her.

He wanted control in that odd way where you wanted the other person to beg, but you also wanted them to jump you. It was complicated, just like everything between these two.

Too bad he was trying to control the one person who clung to control as if it was all she had left in life. Control and lip-gloss was really all Rory needed.

Passion was an odd emotion. With it flowing through your body, you were just as likely to slap someone as you were to rip off their clothes.

She thought about slapping him, leaving a bright red mark on his olive skin, a pulsating heat that he would probably just smirk at.

But she didn't.

She thought about slamming her body into his.

That was definitely the Bacardi talking.

But she didn't. She didn't do anything but stare, at nothing really. She wasn't staring into his eyes or at her feet. She just sat there, until, like clockwork, they were interrupted.

This time, it was her mother. "Lorelai Leigh Gilmore, say goodbye to your friend. And I don't mean the rum. We need to talk."

Lorelai stomped down the hall, her pencil skirt hugging her curves perfectly.

Jess definitely noticed. "Looks like mommy came to save Rapunzel."

"And I guess you don't even have a face a mother could love." The bitch in her couldn't stay at bay for too long.

"Mother is too stoned to notice that I somehow never have dinner with her anymore. And father is fucking Louise's mom, which makes things a bit awkward." Any normal person with feelings would pity the poor boy.

Not Rory.

"I'm sure."

"Say hello to Logan for me." Logan who?

"Tell E I know."

"You know what?"

"Everything."

"How Godlike of you. And I don't fuck E anymore."

"Why not?" Because she hired him to fuck you and you can't dip your dick into warring vaginas. That equaled bad karma.

"I heard terrible things about dicks rotting off."

"Well that makes you less disgusting."

"First you care about me, now you think I'm less disgusting. What's next? You love me."

She laughed even though it wasn't that ridiculous of a thought. Hate was only one step away from love in the book of emotions. "You wish."

"Lorelai Leigh Gilmore, let's hurry! Mommy needs a drink and you obviously need underwear."

"Looks like Mommy Dearest is calling," Jess pointed out.

She shook her head, saying one of the most obvious things that was only said to cut through the tension that was suffocating her in this room. "I need to leave."

"I'm not blocking your exit."

"I know."

"You seem to have a problem with leaving when I'm around."

"Most people have some sort of parting line before they leave." Was she waiting for a declaration of love? She did remember her boyfriend, right? Her unfaithful, loving, stupid, big trust fund boyfriend.

"Parting is such sweet sorrow." When you didn't get fucked, yes it was. Maybe that was what Shakespeare was truly referring to.

She rolled her eyes, not wanting to leave but knowing she had to. "Please, shut up."

* * *

Lorelai had waited long enough for, as Charleston had lovingly put it, her "out of control sex fiend who was addicted to oxycontin and needed a good spanking."

_Jess would probably volunteer to put Rory over his knee and teach her a lesson._

Lorelai was a bit hung over from her martini lunch, and hadn't completely sobered from one of those weird ambien induced trips, so her mood wasn't exactly Mary Poppins esque.

That was why she found herself jerking her daughter away from the one boy who might actually work her out of Logan's slimy clutches.

But she wasn't too sure she wanted her daughter to have anything to do with a boy that might grow up to fuck for a living, whether it be lonely Manhattan housewives or on the set of _Breast Wishes 20_.

Ah, the historic battle of horny and evil vs. horny, charming and evil. Which should a mother prefer?

Lorelai dragged her daughter down the hall, forgetting that her arm was attached to her body. "You smell like a pirate."

"You smell like olives and gin."

"I'm the mother. If I want to spend all day drinking, I can. If I want to not wear panties, I can. But you're the kid. You're supposed to wear panties and not come home flammable."

"Your double standards are so tiresome." Someone was talking like the sixty-year old bitch that we all loved to hate.

"Don't talk like your grandmother."

"Someone has to be the adult in this relationship."

"Well it's certainly not the seventeen year old who loses her panties in Tolstoy. Did _Anna Karenina_ get you that worked up?"

"And you wonder why I never take you seriously."

"I'm sorry. I'm just wondering if I need to put a lock on my medicine cabinet. According to Charleston, I've got some Judy Garland/Marilyn Monroe hybrid on my hands."

"At least I'm being compared to the original sex goddess and not some cheap knock off, like Paris Hilton."

"How are you being so cavalier about this?"

"It's the Bacardi talking." Thank god there weren't any chandeliers or tall buildings around, then.

"If you keep that behavior up, I'll be forced to put you on birth control." Girls who went on birth control were known as notorious sluts. Think twice about that, Lorelai. Your daughter's reputation at Chilton was more important than avoiding an accidental baby. They had other ways to deal with those that didn't involve wearing the slut crown.

"Then I really will be open for business." Jess will be the first in line, riding a unicorn.

"Which means I'll have to either lock you away or horribly disfigure you with a coffee pot."

"Or cut a permanent smile into my face. People don't seem to get too frisky around the Joker."

"That's because he wears the wrong color foundation."

"And a less harsh red might have made his lips pucker."

"Well, we've figured out how to get the Joker laid. Let's try to figure out how to not get you laid."

Rory stopped her mom, who was jerking her away from Chilton like it was the place where virgins went to become women. "I didn't take off my panties in the library."

"Then did you take them off somewhere else and they were planted in the library?"

"You could say that."

Lorelai closed her eyes, not wanting to imagine her daughter becoming like her. "Don't tell me you're a janitor closet slut."

"I prefer Charleston's desk."

"That's it; no more hanging out with Jess for you."

"Think about it, mom. It's classic E."

"I thought E had found Jesus, rode a unicorn and was Hartford's new Diana?"

"It's called being heavily medicated."

"And I had such high hopes for that girl. It really is a shame that you're going to kill her, metaphorically speaking, of course."

Rory brightened. With her mommy on her side, well, that really didn't matter. But it was nice. "So you believe me?"

"I'd be able to tell if you were no longer a virgin."

"How so?"

"You can just tell."

For one, Rory kept her shirt buttoned up to an appropriate level. And two, she still had her panties on. That was how any mother could tell.

* * *

Jess tossed the empty Bacardi bottle into the trash. It had been a rather productive day in detention.

A few more encounters like that and he might be able to produce a grainy, camera phone shot sex tape.

Of course, he was too much of a gentleman to ever share it, but it would be nice to have that little memento from fucking Gilmore.

He'd make sure he was buried with it, since he didn't trust E. She would make sure all regularly scheduled programming was preempted to show the world the day Gilmore's London Bridge came down.

Not that he wasn't still a part of her little game but some things he wasn't willing to share with the Princess of Darkness.

Speaking of her majesty, her claws flew over his eyes in an attempt to be adorable.

Unless she was going to bite him, he had another pair of hands he wanted covering his eyes.

"Guess who."

"A house hasn't fallen on you yet?" He shrugged her hands away from his face, not even trying to be inappropriate.

Uh oh, E. Looks like you're the one with the rusty game.

"You smell like Dolce Vita and a pirate. How was Rory?"

"Quite vocal."

"Bullshit."

"She would not shut up. I could barely concentrate with all the screaming and panting."

"Sometimes I wonder how you get so much ass."

"Do you need a reminder?" He grabbed his belt buckle, teasing E and the entire female population.

She placed her hand on his belt buckle, stopping his movements. "Once was enough for me." And if it wasn't, Jess' dick was all over the internet. Every girl had instant gratification at her fingertips.

No wonder Miss Fischer never went out on Friday nights. All she needed was a bottle of wine, google and her OhMiBod.

The only question was, did her OhMiBod vibrate in sync with Madonna or Marvin Gaye? Oh the choices.

Lorelai preferred her Lelo Golden Vibrator and Casino Royale. Who needed vibrations in sync with Marvin Gaye when you had Daniel Craig and 1500 dollars of pure gold pleasure?

Women in Hartford definitely weren't lacking in the pleasure department between Stella McCartney trunk sales and Swedish vibrators. It made you wonder why penises were so coveted.

_Maybe it was the part that involved dick going into vagina? Just a guess._

E popped a massive strawberry bubble in his face. He hated girls who smelt like strawberries or vanilla. It was so pedestrian. "So how are things going with Rory?"

"She enjoys Bacardi. And my company."

"How long is it going to take you to get up her skirt?"

He shook his head at her stupidity. This wasn't a fuck and run. "You can't rush this process, darling."

"Could you hurry the foreplay up a bit before…"

He finished her morbid thought for her. "You end up at the bottom of a river somewhere?"

"I'd laugh but it might happen. So hurry the fucking up."

"I didn't hear a please." He was too used to girls begging. Rory would certainly be a wake up call for him. No wonder he enjoyed the chase so much.

"Please hurry up the fucking process."

"Thank you."

E studied him for a moment. He looked happy and not in that 'I just got fucked' way but in that 'I might like someone' way. "You're not falling for her, are you?"

"We're not having this conversation again, are we?"

"Humor me. If it's not true, say no."

"She's manipulative, cunning, deceitful and all around awful. Of course I'm in love."

"I love it when two despicable people mate."

"Then you must get excited every time you have sex."

"I should slap you for saying that."

"But you know I'd like it."

"You're sick."

"So I've heard."

* * *

_Of course I'm in love_.

He had to be so full of shit, Rory told herself.

She had run back inside because she forgot her Kate Spade bag, which was one of those things she couldn't live without. When she saw E, she stopped. She didn't want to murder her on school property. The blood wouldn't wash out of the wood floors as well as she wanted it to.

She couldn't stand to go to a school that was stained with E.

She would wait. Jess and E would go off to some closet if they were going to fuck.

But then she heard _her _and knew who they were talking about.

And of course, she had to listen. And she hadn't liked what she had heard.

If Jess loved her, that was it. Nothing would end the way it was supposed to.

Logan wouldn't be her Cary Grant.

She wouldn't ride around Italy on a moped.

She wouldn't get everything she wanted because Jess would ruin it all.

But why is that, Miss Gilmore?

Maybe it was because she wanted him to ruin it all. She wanted him to take her, fuck her and send her back to Chilton looking nothing like Holly Golightly.

Her head hurt from all these ridiculous thoughts. She was a Gilmore. Gilmore's didn't act like this; they didn't fall for boys who carried books around in their back pockets and seduced virgins with Bacardi.

She needed to go talk to Dr. Adams. And get a refill on her Prozac.

_Oh eavesdropping. How we love thee._

* * *

**Ending Author's Note**: I got the inspiration for writing an 'I Never' scene, shockingly (if you know me), from a Skate scene on Lost that I watched about eight hundred times.

And the 1500 dollar Swedish pleasure device does exist. If you want one, I can link you. There is also a talking one you can program with different voices.

**Reviewers**: I just have to jump up and down on a couch on imaginary Oprah and tell the world how much I love ya'll. Ya'll really let me do whatever I want and make these characters as awfully awesome as possible without complaining. You guys own. I hope this chapter continued the tradition of being so bad that it's awesome. If I'm addicted to it, you should be too. It's like Pineapple Express: the dopest story you've ever smoked.

Or something like that.

And reviews are yummier than Bacardi.

And (again) sorry for the slow time between updates. Every time I go to write a chapter now it becomes this big historic event that takes over my hands and I can't stop until I bleed myself dry. Maybe it's a good thing I'm going on "vacation."


	5. Love Is Colder Than Death

**Chapter 5**: Love is Colder than Death

**Author's Note**: I noticed I used the work 'fuck' a lot in this chapter. It's not because I'm like "Watch me be cool and dangerous by having a potty mouth!" I just really like the word. Frak is nice and all (I use it in front of grandma) but nothing beats a good fuck. And you know you're thinking about double meaning right now.

**Disclaimer**: The title belongs to _The Virgins_. Proper band for this story, don't you think? But yes, they own its brilliance.

* * *

If you heard a boy say the words 'of course I'm in love' (in reference to you) your next obvious step would be to run off and fuck another boy, right?

No?

That wasn't how Romeo and Juliet got together?

Didn't you need to play hard to get (and it was certainly hard to get you when someone else's dick was occupying your vagina)?

It appeared Rory Gilmore wanted nothing to do with love, at least not the kind Jess Mariano had to offer.

_It couldn't make her anymore itchy than Logan's love stains would. _

She'd rather lose her virginity to her boyfriend's wandering penis.

She'd programmed it into her blackberry.

Made a checklist of things she needed to do in preparation to become just another Chilton slut.

Go on the pill.

Max out her credit card on garters and bow bras from Tanga.

Not eat for an entire week.

Forget about all those pesky sex dreams she'd been having about Jess Mariano.

_Wait, Snow White was letting everyone's favorite dwarf violate her? Tell us more!_

One minute, she'd be dreaming about frolicking around in a vintage Nolan Miller cocktail dress; the next, she'd be tied to her bedpost with two silk Hermes scarves around her wrists. Her little black dress would be bunched up around her waist because, shocker, Jess' head would be buried in her white lace panties.

_Oh my_.

It was all very over the top (and a bit S&M, obviously) but she always woke up with her silk chemise clinging to her body.

She knew something had to be done when, one night, she found herself on top moaning like a porn star.

And she was wearing one of his favorite Burberry ties around her neck.

She immediately popped a few Quaaludes and washed it down with a Red Bull.

_She always had a Red Bull on hand, even at three in the morning. _

Someone obviously didn't have a future as a pharmacist. Why combine a sedative with caffeine?

Unless she was addicted to being sedated. Or maybe she thought being sedated would stop the sandman from delivering thrusting.

She was positive that her subconscious was just telling her she needed to get laid and had confused the dark, horny, charming asshole with her asshole.

Now she just needed to tell her boyfriend she was ready to be ravished.

_Nothing got a guy harder than ravishing a virgin_.

She applied a few squirts of Burberry London on her pulse points. She'd chucked her Dolce Vita because she was wearing it the day Jess decided to act like a fucking moron.

Besides, she needed a new scent since in five hours she was no longer going to be the Chilton Princess.

Five hours. Jess might not even be able to cock block this one.

* * *

Now came the painful part, if you forgot about the fact that no one enjoyed the pain and humiliation of their first time.

And that it was well known that Logan couldn't please a plastic vagina, much less Rory's picky one.

But anyways, it was time to tell Lorelai.

Rory was prepared to have her Zac Posen French lace top stained with coffee because when Lorelai was unhappy, she tended to channel Joan Crawford.

Translation: Douse her sex fiend in hot coffee.

Rory had chewed her nails down to the point that a French manicure couldn't even save. Time to spit it out before she ate her entire arm.

But at breakfast, when cinnamon rolls were on the table? Cinnamon rolls were supposed to make people happy.

"I'm going to lose my virginity in five hours," she stated, like it was something to be proud of.

This really wasn't a thing you discussed over breakfast. There wasn't enough alcohol on the table.

"Greta, bring me the bottle of Absolut." Lorelai was about to fix that tiny little problem it appeared.

"You knew this would happen someday." Since that was the main option people used for reproduction, Rory had a point. But no sane woman celebrated with her daughter when she was about to get banged for her very first time.

Hallmark didn't make a card for that for a reason.

"It won't be happening in five hours."

Lorelai hated when her mind went to that place where she asked herself what would Emily Gilmore do. She hated Chanel No. 5 and botox, so she loathed her mental freaky Friday moment.

Emily would probably approve of the copulating if it involved Logan.

"You can't cock block Logan." Oh yes she could. All she needed was a wire hanger or a Playboy bunny. Then Logan wouldn't be getting any from her daughter.

She'd prefer for him to impregnate some slut than fuck his way into her family.

He probably didn't know to aim right.

"Oh, so it's Logan who is going to be riding in on a white horse and poking you with his sword?"

It took more than a poke to do the job, Lorelai. Didn't she remember her first time on Charleston's desk?

_If Jess had it his way, history would repeat itself._

Rory would have been hurt by her mother's subtle accusation if she actually had feelings.

Um sweetie, you were the one who was drinking with other boys. "Who did you think it was?"

"It doesn't matter. I'm scheduling you an appointment with Dr. Adams." Ah, the famous Emily Gilmore tactic: when your child wants to have sex, send them to a shrink.

It didn't work out so well for Emily, if you hadn't guessed.

Again, rage blocked reason. It didn't matter that sex with Logan made her want to vomit; she was going to do it and no one could stop her. "I'm not crazy to want to have sex!"

"Yes you are. This is insane behavior. Have you been abusing Quaaludes again? Or did someone give you some coke? Oh my god, you're sweating. You're on drugs again. You are not going to become a coke whore!"

Okay, Rory might have enjoyed snorting a bit more than your average heiress (who were we kidding here; every heiress shot it up her nose), but she didn't appear to be the type of girl to fuck for coke. That was E's line of work.

"Mom, it is just sex! I thought you'd want to know."

Open and honest relationships were so not in. Buy your debutante the Louis Vuitton Patchwork bag and stuff it with condoms. That was handling sex. Talking about_ it_ was almost as bad as asking your mother for tips.

"I'll buy you a vibrator. Or porn. But no sex. Ever."

Rory crossed her arms over her chest, protecting her lace top and pretending to pout about having a porn fashionista for a mother, all at once. "You can't make those kind of rules."

"You told me just the other day no one was taking off your panties." Maybe she'll be the one to take them off. Or better yet, why wear panties?

Oh yeah, the build up.

"Logan and I have been dating for four years." Man, Logan really must have gotten lost in the detour to her vagina. No wonder he fucked all those Chilton vaginas on a stick.

"You don't even like Logan anymore."

"Every relationship goes through periods of…" she trailed off, forgetting what exactly her and Logan were going through.

Whatever it was, it was drier than Barbara Walter's vagina.

"Mutual hate?"

"At least I'm not off fucking people who aren't my significant other like dad did. Would you be fine with this if I was fucking Jess?" She didn't even blink when she said this. Cold hearted bitch or not, there was such a thing as crossing a line and she'd just done it.

"I'm calling Dr. Adams as soon as I calm down enough to not rip your pretty little head off."

"Dr. Adams supports exploring your sexuality." Can you get a prescription that says 'Explore your sexuality on a daily basis'? Maybe it'll even get you out of gym if you have to explore your sexuality constantly.

"Then I'll send you to a nunnery."

"You're such a hypocrite. You were fornicating anywhere that had something stable to lean against when you were fifteen."

"Don't insinuate that your mother was a slut. It will make her do crazy things, like kill you."

"I'm having sex." Rory was indignant about this. There was no stopping her vagina.

"No you're not."

"You can't stop me."

"I'm not going to. You don't want your first time to be with a boy you don't even love."

"I love…" Rory stopped. If it was the truth, why stop?

"You love yourself and his money. Not Logan. Go buy a box of condoms. Go get a Brazilian wax. You're not going to fuck Logan."

But she might sleep with him just to prove you wrong. She was that vindictive. Especially since Logan had Egyptian cotton sheets.

High thread counts were very attractive.

Lorelai just didn't understand. No one could understand. "Excuse me. I have things I need to do." Rory chewed on the inside of her mouth, stomping off to get the keys to her Beemer.

She was so fucking angry.

How could Lorelai deny her the basic human right to get laid? How could she say Rory didn't love her perfect, Cary Grant boyfriend?

Why was Lorelai always right?

It didn't matter. She had to sleep with Logan because he wasn't Jess.

And that was all that mattered.

* * *

Her panties didn't match her bra. She'd left her black lace garters in the Fed Ex package under her bed.

She smelled like sweat and London.

_So like Kate Moss? _

Her hair had been blown into knots from the ride over in her BMW convertible.

She just had to focus. If she focused on Logan, everything would be fine. He'd get in, get out, it'd be awkward and then she'd leave, unsatisfied, without cuddling.

But it didn't matter. After this, Jess wouldn't follow her into the bathroom or play 'I Never' with her or breathe on her neck, his smell of cigarettes turning her on more than anything Logan had ever done.

She was sure Jess only wanted her because she was a virgin. It was his thing to chase virgins.

_Oh sweetie, sometimes it was shocking how naïve you were_.

She hadn't called before she came over, so Logan could be in the hot tub right now with half the senior class but she didn't care. She'd do it in front of all those girls if she had to.

She wasn't exactly using her brain at the moment, if you couldn't tell.

Rory held down the button for Logan to buzz her up to his penthouse like it was some emergency.

And in her mind, finally sealing the deal with your girlfriend was a big fucking deal. She had worn a see through lace top and kitten heels.

He wouldn't stand a chance. All she needed was a whip and she'd dominate his ass.

"Logan, let me the fuck up! This is an emergency!"

"Ace, is that you?" He sounded stoned. Or blown. Or maybe he was blown and stoned.

"Who else would it be?" A hooker he hired for the day to do his laundry and make him come? Your arch nemesis? His best friend? His dealer? See all the options, Miss Gilmore.

"Well…"

Only the dumbest fuck in the world would answer that question truthfully.

"Logan, buzz me up! I'm cold." Uh, it was like 80 degrees outside. Someone wasn't into foreplay, obviously.

"How cold are we talking?" Logan smiled that dopey Cheech and Chong smile. He couldn't help it. When you were high, hard nipples were even more awesome.

"Stop being a pervert." If this was any hint as to how Rory was going to be during her little sexual experiment, we might as well tune in to Animal Planet. At least the animals got into it.

"You suck at dirty talk."

"Well, right now, you suck at turning me on." To turn Rory on, you'd probably have to fuck her against a stack of old books or recite some passage of Jane Austen while you were thrusting in and out.

Unfortunately for Logan, he'd never quite grasped the concept of reading.

Oh to be rich and illiterate.

"Fine babe, buzzing you up." He wasn't in the mood to have his hand slapped away as he was on the cusp of unhooking her bra today.

Nor did he want to listen to her bitch about how inadequate he was and how as soon as she left, she was going to go fuck all his friends with the year's supply of condoms she'd bought from Costco.

If it wasn't sold and Barney's, chances were Rory wouldn't buy it, so she could only pretend to buy condoms in bulk for so long before Logan called her on her bullshit.

"If anyone is up there, shove them under the bed." Or she would throw them out of the window.

"No one is up here."

"Are you working on that monogamous thing?" Aw, maybe Logan did want 3.5 kids and a golden retriever with Rory.

Along with your standard mistress.

"It's hard to be monogamous when you won't let me touch you."

"Well maybe we'll have to change that," she responded coyly, before entering the elevator to his penthouse.

This should be interesting.

* * *

If you didn't know it was Rory Gilmore, Audrey Hepburn wannabe, future DAR bitch, you'd think Logan had hired a lady for the afternoon. There was no kiss on the lips. No slap to the face (although depending on what Logan's fetish was, that wouldn't rule her out as being a lady of the night). No ordering of caviar, champagne and strawberries.

She eyed his golden chest, perfectly waxed because water polo players were just a tad bit gay. And there was something about being aerodynamically something, but honestly, boys waxing each other and frolicking around in water only conjured up images of boy bands and Project Runway.

"Take off your pants."

It wasn't good to shout commands at someone when they were slightly stoned and in need of a bag of Fritos. "What?'

She rolled her eyes, knowing why, if she could, she'd fuck herself. She was brilliant, beautiful and filthy rich. Everyone else was just a disappointment. Too bad it'd be weird if she ran down the beach into her own arms.

Maybe Dean or Bleam could help her with that cloning. "Do I have to do everything myself? Take off your pants!"

He blinked a few times, finally realizing his girlfriend was wearing a completely see through lace top. And somehow, she'd ripped his bong water stained t-shirt off. Did she want to have sex? No. She couldn't be giving up her virginity just like this. The day she finally decided to consummate their relationship, he'd have to dress up like a hobbit and go on an adventure in search for the key to her chastity belt or some shit like that. It couldn't be_ this_ easy. "I'm confused."

"We're going to have sex," she stated slowly, unbuttoning the first button on her Zac Posen blouse.

"Fuck off." Wow, not the right response at all.

She shoved him onto his bed, deciding that she would have to do this all herself. She'd taken sex ed. She'd watched _Body Heat_. She could do this, even if she had to guide his penis the entire way.

It was a good thing she was flexible or her current position would certainly cause her to pull something. "Rory, you're straddling me."

She felt nothing. No erection pushing against her. Nothing. "Why aren't you hard? Shouldn't you be hard?"

"I'm stoned." Marijuana had the same effect as cold water.

"Do I need to do something to get you hard?' She figured a hand job couldn't be too hard, right? And he was wearing pants, so nothing would get on her five hundred dollar top, thank god. Semen ruined everything.

"Your mouth might help."

She immediately frowned at the thought of giving him a blowjob. Talk about undignified. She was way too good to take part in an activity like that. And swallowing? Only sluts swallowed. "Um, no. I'm not into that."

"I'm kidding babe. Did you do some coke or something before you came over here? Your pupils are super dilated."

"I'm straddling you and you want to talk?" She stopped, a sob enrapturing her chest. It wasn't like this in _Love Story_! They were so in love. And he probably fucked her all the time.

And then she died. Dream big, Rory.

"Why won't anyone fuck me?" Chanel Inimitable mascara dripped down her neck. She'd succumbed to ugly crying, her face blotchy and red, snot dripping out of her nose.

It was super attractive.

Logan sat them up, leaving her on his lap. First she wanted to do it, with her on top, by the way, and now she was a blubbering mess. Maybe she really was bipolar. "Whoa, whoa, please don't cry. Slow down. What's going on?"

"Nothing," she hiccupped, "is wrong."

He brushed a few pieces of hair out of her face, leaving a kiss on her temple. He was trying to appear sensitive and understanding. He was trying to be the perfect boyfriend. Too bad he'd failed miserably the first four years. But maybe he had more control over his penis now.

"You're crying."

She pushed his hands away from her face, not wanting an intimate, loving experience. She wanted him to fuck her without being a sweet, perfect boyfriend. God, didn't he understand? "Because you won't take your pants off!"

"You want to have sex now?" Normally girls who cried before sex weren't the ones you wanted to fuck. Date rape was such an annoying crime.

"This isn't the Special Olympics of fucking. Please, catch up." She pushed him back down on the bed, attacking his face in something that resembled mauling more than kissing.

He tried to turn his head so she could at least give him a hickey instead of poking his eye out with her darting tongue, but she was not getting his subtle hint. "Rory, you're eating my face."

"Cosmopolitan said I needed to be aggressive." One cannot argue with the authority on relationships and sex. If Cosmo said do it, you must obey, no matter how disgusting and slightly illegal.

Wasn't he supposed to be doing the ravishing?

Right now, she was more like the witch from Hanzel and Gretel than those hot, sexy singles you ordered online.

_Rory was aware he wasn't made of candy, right? _

He pushed back, throwing her off the bed and onto the floor. Coordination really wasn't their thing.

"Sorry, Ace. I was trying to flip and…" And you threw your ninety-pound girlfriend into the air. Brilliant!

She noticed a red liquid gushing out of her knee. Well, no one ever said your first time was easy. At least she'd have a battle scar to prove she did it. "I think I'm bleeding."

"Shit, really? Where?"

"It's okay. It doesn't hurt that bad. I can get through this," she stood up, ignoring the red stains on her porcelain skin. A little blood never hurt anyone. Besides, if Angelina Jolie and Billy Bob Thornton got turned on by each other's blood, Logan might do the same, if he was a vampire.

If they ended up wearing a vial of each other's blood around their necks to prom, be worried. It wouldn't be a big deal if they had sex in the limo, but blood around their necks would be so unsanitary.

"Sex isn't something you're supposed to just get through."

She wanted to laugh in his face. Sex was undignified, painful and sometimes, boring. It wasn't something she was going to invite the Dallas Cowboy cheerleaders to witness.

There wouldn't be any one, two, three 'Gimme an O!' cheers.

"Come on Logan, just fuck me," she whined. "I have an appointment with Dr. Adams in an hour."

"No."

She must have misheard him. No one said no to Rory Gilmore. "Please, you've been begging me to do it with you ever since you found out where your penis would go."

"You don't want to do this. I don't know what's going on with you, but I'm a bit above a pity fuck, if you hadn't noticed, sweet cheeks."

"Do you want me to beg?" She tried to give him a kiss on the lips, something to get the blood flowing to the right place.

_That would be Viagra, sweetie. Check Mitchum's study. He surely would have a few tablets on hand. _

Logan wanted nothing to do with her. He pushed her back, hoping she'd trip and fall into a rabbit hole lined with Prozac. "No, I want you to leave."

She stumbled back a few steps. This wasn't how this was supposed to go. "If I leave, we're over."

"I'm not really into ultimatums."

Who would of thought fuck me or we're over would have been a bad ultimatum?

"You're such a dick. Do you know how lucky you are to be with me?" It depended on what your definition of lucky was. If your ideal match was killer legs, red lips and psychotic tendencies, then yes, Logan was the luckiest motherfucker alive, after John Mayer.

He smiled that perfect 'I'm a rich asshole' smile he had been using since kindergarten. Even when he ate glue, he was superior. "I'm a Huntzberger. I can have whomever I want. I believe you're the lucky one."

"Yes, four years of not being satisfied makes me the luckiest girl in the whole wide world."

"You don't even try, so don't put this all on me." Well, offering your body was kind of trying, even if she didn't mean it.

She bit down on her chapped lips to keep herself from crying. She preferred to bottle up any emotion that wasn't filed under 'crazy bitch.' "I don't know what I was thinking."

_That Jess liked virgins and you were a virgin? _

"You've been ignoring me since your mother's party and then you just show up here and want me to fuck you and you're the one who's mad?" Again, when did Logan become morally superior to all of us?

"I get to be mad."

He knew if they fought much longer, he'd be doing her on top of his Xbox. The only good thing that came of their fighting was that it generally got him to second base without having to say please. But today he was too stoned to want to do much with her. "Whatever. I'm not in the mood to deal with your shit today."

"Go fuck yourself." Don't use the nice towels! They will never be soft again if you whack off into them.

"I will and then I'll fuck E, because unlike you, she actually knows what to do."

Her hand went flying through the air, immediately making contact with his jaw. "I hate you," she spat out, angry tears flooding her eyes.

He grabbed her wrist, pressing his fingers into her hand as a warning to not try and slap him again. "The feeling is mutual, darling." He tossed her yellow submarine colored Coach clutch she'd laid on his bed at her, practically shoving her out of his penthouse. "Dr. Adams really needs to up your medication."

"I hope your dick falls off." Well, E was the black plague of vaginas.

"You've gotten boring lately, Rory. And don't think I didn't hear about E finding your panties in the library." Was that before or after he did Madeline in sacred stall number 2?

"So that's what your little fit is about?" No matter how many girls Logan bedded (or did against a hard object), Rory couldn't do anything but sit at home and pray to the Chanel Gods.

Possessive much?

He held her wrist a bit tighter, like he was trying to remind her that in his sick Logan way, he owned her. "You know I don't like to share."

"Neither do I." Oh Rory, you were so ironic.

"I guess we have a problem, then." Then either kill each other or break up!

"That's all we have in this relationship."

This time it was him whispering in her ear. She hated how he always smelled like pot and dick. He could at least figure out that his natural musk was not attractive. "And you fucking love it. You can't be with someone and actually be happy. It's not in your DNA."

Thank you for the psychoanalysis, Huntz.

"Well you sabotage any chance we have with every passing vagina." Or maybe he kept them in his closet now.

"If you hate me so much, leave." He gave her a little push toward the door, knowing she'd be back for more once she figured out Jess or whoever was messing with her perfect little fantasy world where she was Holly Golightly, got what they wanted, aka, pussy.

"Gladly."

* * *

Rory carried the look of a girl who had tried to have sex with herself, but had run out of batteries. And then somehow, she had fallen on top of a large, black woman who had beaten her with an umbrella.

_Right. _

Her face was trying to pull off that tragic look of a girl who didn't own under eye concealer but loved to cry her eyes out.

Everyone knew it took a lot of makeup to look natural, so she just looked like a homeless freak that had wandered into Barney's and gotten lost in a Zac Posen top.

She waited for the elevator in the lobby of Dr. Adams office, praying she didn't see any of her fucked up friends when she wasn't even wearing shoes.

_Britney Spears much?_

_Couldn't she have gotten Alfred to stop and buy her a pair of Manolos? Bare feet made her seem poor. _

The dinging of the elevator was her savior from ending up on Page Six again. She hadn't graced that trash column since the time she crashed that awful party Finn's parent's threw for his sixteenth birthday. Who knew wearing a see through chemise and carrying around a champagne bottle with something under your nose that wasn't powdered sugar would make the gossip bitches come all over their blogs?

She heard someone calling after her to hold the elevator. Too bad Rory didn't wait for anyone.

_That might make sex a bit unsatisfying_.

Her finger held down the 'close door' button, praying (man, she was really into God today, which was odd since she normally only worshipped Valentino) whoever was slamming their feet into the ground were here because they comforted themselves with food and would be too fat to fit through the tiny opening.

He slid between the crack, a blur of black leather and hair gel, his Burberry tie slapping him in the face.

Rory would have laughed if it weren't _him_.

_Leather and Burberry? Only one boy in Hartford could get away with looking like the bastard son of Prince William and James Dean. _

"Oh you've got to be kidding me." She reached into her clutch, extracting a cigarette. "Fuck, I don't have a lighter."

Jess ran a hand through his hair, mentally blowing himself for how brilliant he was. "No smoking in elevators, dear."

"When have you ever followed the rules?" The bad boy thing was kind of what got him all that ass.

Oh yeah. And his ass.

"As much as I love a good spanking, the security guard out there doesn't seem very frisky." That was because she preferred surf, not turf. And she already carried a gun. Didn't need another one

"She'd probably love to frisk you."

He put his hand over his heart in an overly dramatic gesture Lance Bass would be proud of. "Are you giving me a compliment?"

"Just stating the obvious. Women who are dying for a little attention succumb to your charm." She rummaged through her purse, hoping to find a lighter, a sedative or an anvil to drop on her head. "I didn't know you saw Dr. Adams."

"She helps me with my issues."

"I don't think being a slut is an issue." At least he hadn't started having sex for money. Yet.

He laughed. "Why don't you like me?"

She frowned at him. She couldn't lie and say she didn't like him. She couldn't lie and say she did like him. So she opted to be evasive. If it worked for brooding bad boys, she could certainly do it. "At this very moment? Because you won't give me a light and I really need a cigarette."

"I can tell. Did Barney's not accept your credit card?" She'd be in jail for killing a sales clerk if Barney's had denied her in front of _common_ people, duh!

She didn't look him in the eye, instead staring at her bare feet. Her cherry polished nails were chipped. Probably from kicking Logan's door ten or fifty times. "Logan and I... we...had a fight," she struggled out.

"About me?" Smug asshole of the year award goes to Jess Mariano. Line up to knee him in the nuts, ladies.

At least if he was sterile there would be less smug assholes.

_Well, there'd still be Logan and his ten illegitimate children. _

"See, this is why I don't like you. You assume everything is about you. You're a pompous, arrogant, over gelled ass and you would suck your own dick if you could reach it because you're so in love with yourself." That'd take a lot of bending and grunting to make that work. It would be a you tube sensation!

"Well if I was choosing between myself and you, of course I'd choose myself."

"I am not an option," she reminded him. Unfortunately for her, being alone with him in an elevator could only lead to trouble.

He stuck his hands in the pockets of his Calvin Klein black stripe suit pants. "You and me, we're a lot more alike than you want to admit."

"We have absolutely nothing in common." Except for a love of books, being insanely privileged and most importantly, being ridiculously hot without trying.

"You'd fuck yourself if you could. That's why Logan and you won't ever work. He doesn't get you." If he didn't slow down, the dreaded soulmate word was going to escape from his lips.

She scoffed. "And you do?"

Jess leaned back into the stop button, bringing the elevator to a halt. For every pair of Givenchy pants Dr. Adams bought, she was too "cheap" to replace her Tower of Terror model of elevator with something modern.

Rory would be burning her pants right off with the death glares she would be sending her for this terrible, unfortunate, possibly awesome circumstance.

_What, you've never seen what happens in stopped elevators on Grey's Anatomy? Or moving elevators. Really just any elevator. _

Instinctively, she started backing into the nearest corner. "You can't stop the elevator!"

A step forward. "I just did."

"Stopping is for emergencies." Sort of. But what is defined as an emergency? Two hot people needing to do it is sort of an emergency.

"This is an emergency. Of the heart." Whoa, pulling out his inner Mr. Darcy.

"If you knew me so fucking well, you'd know I was claustrophobic." And obviously Rory will be reprising her role as Miss Bennet.

Another step. "One little kiss."

She hadn't expected that. She'd expected she would have to beat him off with her yellow submarine clutch. But not for him to ask for a kiss. Jess wasn't the kind of boy who asked. He just took, like the Cookie Monster. "What? What is wrong with you?"

Now he had her pined in the corner. Unless she said 'excuse me' like the society girl she was supposed to be, there was no escaping this without a little scuffle. "A lot of things, obviously. That's why I'm in therapy.'

She averted her eyes from his, staring at the fascinating shade of white on the walls. "Why do you want me to kiss you?"

"Because you haven't been properly kissed."

"How would you know?"

"I have a sense about these things. The most action you've gotten was from your pillow in sixth grade." What a lucky pillow. Maybe she had Johnny Depp's head taped to it.

"I'm not kissing you," she said in that tone that told you she could be easily persuaded if you offered to take her to Bendels afterwards and spring for an extra shot in her latte.

_Ah, 20th century romance. _

"Don't you want to prove me wrong?" he challenged her. Rory was the most cutthroat bitch he knew. She couldn't let him know she was scared of what would happen when she kissed him.

"I hate you."

"Which is almost like loving me."

"That makes no sense."

"It doesn't have to." He placed his hand at the opening of her blouse, running his finger back and forth under the material. It was the simplest of touches, but her skin was turning a bright pink with just that bit of contact. "You're blushing."

"No I'm not." Then someone must have colored her with a really big Crayola crayon on the way over to Dr. Adams office.

He moved his fingers to her collarbone, loving how at every touch, she got brighter and brighter. If he didn't stop, she'd be mistaken for Rudolph. "Your whole body is blushing."

"Stop touching me."

"Am I making _that_ part blush too?"

"You're such a pig."

He pulled his hands back, satisfied with molesting her neck for the day. "Why aren't you starting the elevator?"

"What?"

"You could press the button to start it."

"I…well…my…" Use your words Rory!

He smirked at her inability to form coherent thoughts when he touched her. "You're stuttering."

"Would you stop telling me what I am doing?"

"One little kiss and I'll leave you alone forever." Only if it turned out she was a man would he leave her alone. And even then he might stick around depending on how into vagina he really was.

"One kiss?" For some reason, she considered this proposition.

"My lips laying on top of yours for half a second." That was true. Your lips didn't have to make much contact during sex if you were Rory Gilmore.

"I don't need the definition of a kiss, Webster."

"Aw, look, we have nicknames for each other."

"No, your nickname is Asshole."

"Such a term of endearment, Freckles."

She sighed. "Why do you want one little kiss?"

"Call it a late birthday wish."

He leaned his forehead against her crumpled form, an act more intimate than anything he'd ever done with the French whores, Chilton sluts or lonely Hartford socialites he'd fucked, just letting his nose rest against hers.

Giving her the option of where to take this.

It was an Eskimo kiss, a reminder of that first spark they'd felt back at her mother's party. Nose humping she'd called it. But this time gonorrhea boy wasn't lurking.

It was their moment in a stopped elevator to do whatever they wanted.

Or needed.

'Just one little kiss' she told herself. Just the brushing of his lips against hers.

It would mean nothing.

She didn't know what do with her hands. They were shaky, wet, unsure. She didn't want to touch his because that was too intimate. There had to be as little touching as possible.

She just left her hands at her sides, dropping her clutch to the floor.

Her eyes held his for just a moment. What was she trying to communicate? Fear? Panic? Longing?

All his eyes conveyed was an intense lust, his chocolate brown replaced with a cold, hungry, lost black.

She grabbed his bottom lip with hers, but just for a moment, before pulling back. Simple. It was a simple kiss.

_But wasn't that the definition of one little kiss? _

But then, something happened.

Fuck pro/con list. Fuck Logan (not literally) and Emily's china patterns and being valedictorian and every other rational thought she had made in her entire life.

They collided in that perfect collision of need, want, fear and lust. She surprised him. He never thought he wouldn't be able to keep up with her, her obvious need for control apparent in the way she had pushed him closer to the wall.

He was in the corner. She was the one who always backed up, always ran away. But with her hands around his neck and tongue in his mouth, she wanted this just as much (or more) than he did.

She was sour, bitter, salty, which was perfect because he hated the sugar and spice and everything nice girls.

His hands found their way back to her lace top, sliding the material off her shoulders. He just wanted to touch more of her, any part of her. His callused hands rubbed circles into her ivory skin.

Electric. She felt that cool electricity pulsing through her veins. All she had at this moment were feelings. Not thoughts, just basic, animalistic feelings.

She bit down on his lip, drawing blood. The cooper taste swirled in her mouth, but she didn't stop. If thoughts didn't wreck this moment, she'd bleed the poor boy dry.

He put his hands on either side of her face, moving her back into the corner. He slowed it down, wanting it to last longer than he knew it could.

He didn't want to stop to breathe. He didn't want her to have time to think. Things were better when Rory didn't think.

_Obviously_.

This moment was per…Stop.

She heard a banging sound against the metal door of the elevator.

And it all came back to her. She was in a dirty elevator and her tongue was currently occupying the mouth of that stupid, stupid boy.

Motherfucker.

He felt a pressure on his shoulders. He knew that touch. Rory Gilmore was doing that thing where she used her brain.

He really hated when she did that.

There was no slowly pulling away, no forehead rest, no dreamy stares. Rory was too disgusted with herself to be sentimental. "Happy birthday, you jackass."

"I just asked for one little kiss." And you got a boner. Lucky you!

"That was a mistake."

"Methinks the lady doth protest too much."

"Logan…" Oh come on. Why be faithful to someone who wouldn't do you? Go to the dark side, where it was sweaty, in a good way.

"Doesn't deserve you."

"Neither do you."

"I might not but from that little show you put on, you obviously want me."

It was the second time today she'd slap someone. This one was much more enjoyable.

He nursed the red mark her hand had left on his jaw, not angry. Not frustrated. He was totally turned on. "You could have just told me you wanted it like that."

"I don't want it anyway from you."

"Was it that bad for you?"

"Why do you care as long as you got off?"

"Well, I was just looking for a little clarification because moaning usually means you're enjoying yourself. But I guess not with you." He smirked. "And how do you know I got off?"

_Besides the obvious bulge daring to rip his Calvin Klein pants? _

She restarted the elevator. She didn't trust herself with him and his hard on any longer.

* * *

Dr. Adams was the psychiatrist who had convinced Lindsay that trying out Samantha Rosen's fur burger would be good for her.

She'd made Isaiah Washington love gay people (just not in time to save Grey's Anatomy, but that show was bound to self destruct sooner or later).

She'd made countless "lost" celebrities find Jesus or something else to worship (for Oprah, it was giving away shit and her va-jay-jay).

Emily Gilmore called her a miracle worker, the Hartford version of Annie Sullivan if Annie wore Givenchy patent leather stretch trousers and had fucked more men than Sienna Miller.

_And she was the authority on relationships? _

Emily was certain she walked on water to get to her office everyday and could turn water into a 1998 Pertus Pomerol, the wine of choice by the Kennedy's, who were royalty in the eyes of the Gilmore's.

That was why she was chosen to be Rory's therapist after the Chris incident. You see, Rory had walked in on her father finding out what Victoria's Secret was with some model that definitely wasn't Giselle.

Maybe if her dad had chosen to stray with a Gucci model or Giselle herself Rory might not have become best fucking friends forever with E. But he didn't; he chose to use some no name Brazilian slut to ruin his family.

The bitch didn't even know who Oscar De La Renta was. Thank god she hadn't become Rory's step monster.

No wonder Rory had an aversion to sex. Seeing your dad being rode by some Brazilian wouldn't fall into the realm of awesome.

_At least he wasn't gay_.

Dr. Adams pushed her icy blonde hair behind her ears. Uncomfortable wasn't a strong enough word to describe her session with Miss Gilmore.

Rory was just sitting there, like one of those sad little kids with leukemia who held their teddy bear and didn't have hair and should be on a milk carton or something.

Or she just looked retarded, with that gaze to nowhere. Dr. Adams was afraid she would start drooling at any second.

She probably didn't have to worry about drool on her Persian rugs. Rory had shared all her saliva (and her peppermint gum) with Jess in the elevator about ten minutes ago.

"Your mother tells me you want to have sex."

"She's misinformed."

Dr. Adams crossed her legs in that disturbing _Basic Instinct 2_ way, meaning she was way too old to not be wearing panties. "So you can speak."

"I'm paying you five hundred dollars an hour. If I want to sit here and say nothing, I can. You still get paid. It's not like you're a whore and if you can't get it up you have to give a refund."

"Actually, your mother pays me."

"Do you think I do not realize that?"

Dr. Adams knew this was going to be one of their historically bad sessions. Not that Rory was normally a ray of sunshine to deal with. But today felt like a repeat of the time she had mixed ecstasy, a double shot espresso and no sleep. She cried the entire time then passed out for five hours. Emily was not impressed. "How is Logan doing?"

"I don't know." No Rory, you didn't know **whom** he was doing. Different question!

"Did you two break up?" Way to be Miss Sensitivity there, doc. She did realize she was treating a manic-depressive, right?

"I don't know."

"Why don't you know?"

"If you kiss another boy does that mean you're broken up?"

We should all kiss a boy who wasn't ours once in awhile.

"That's a complicated question."

"It's a yes or no answer." Unless you were planning on moving to Utah and being a polygamist.

_Big Love _had complicated everything. Damn HBO and cults.

"Well who was the boy?"

The society version of James Dean. Pretty much perfect in a pair of Marc Jacobs jeans.

"No one important." Rory watched as Dr. Adams took notes. She hated being gawked at like she was some science experiment. Why the fuck was she in therapy anyways? She was perfect.

_Perfectly fucked up. _

"Then it probably doesn't mean anything.

"So I can just go around kissing random boys and it's okay?"

"That's not what I meant."

"That's what you implied!"

Dr. Adams took a breath. She didn't need Rory trying to strangle her. Again. "Do you care for this boy that you kissed in anyway?"

She cared when she was drunk on rum. And they say you're at your most honest when you're sloshed.

"He has potential."

"What does that mean?"

She sighed. "If he wasn't such an asshole, he wouldn't be completely awful to have feelings for. But he'll always be an asshole. So it is not even an option to develop feelings for this boy."

"Who is this boy?"

"Jess Mariano."

Dr. Adams couldn't let another one of her patients fall victim to his lecherous charms. "You can't kiss Jess Mariano."

"If he was fucking your daughter, I can assure you it was nothing special." Way to dash any future mother-in-law dreams she had.

"He's not a nice boy." But nice guys finished last, behind prisoners because they shanked them. And conjugal visits were hot. Tell your friends. It was a thing now.

"And you think Logan is nice?"

"I've never met Logan." That was because you had old pussy.

"You're lucky, then. Logan has a Ph. D in fucking up."

"Have you ever considered the fact that you might enjoy self destructive relationships? Your mother was known to choose the wrong man over and over." And it got her a seventeen-year-old bitch and enough money from divorces to buy all the Prada bags she could ever need. Picking the wrong man did have its advantages.

"I just kissed a boy in your elevator. A boy who is not my escort for my debut into society. A boy who has been up every single skirt at Chilton and probably every neighboring county. You don't think I know how self destructive I am?"

"You kissed Jess in my elevator?"

"It was just a kiss. You don't need to disinfect it."

"Jess is way more dysfunctional than he lets on. His issues run much deeper than just being…"

"A slut?"

"Yes."

Even though Rory didn't want Jess, she didn't want someone telling her she should stay away from him. That just made her want him more and she hated that feeling. "When your daughter was found swimming in the fountain at Barney's in that awful Versace gown, was it because Jess had screwed her?"

"Excuse me?"

"You seem bitter about Jess. I don't think it's very professional to hate your client. Or to treat the person who took Kate's virginity, do you?"

Dr. Adams wanted to call security to escort her little out of control ass out of the building. She needed to be sent to finishing school. "I think we're done here."

A professional might say Rory's need to be a bitch at every possible moment was a defense mechanism.

Sadly, she wasn't that complicated. She just loved being a mean girl. It was way more fun than playing Mary Sue, especially when you got to stab people in the back with your Kate Spade heels.

"Now refresh my memory. Did you really send Katie off to France because she was prodigy in being a slut?"

"I'm calling your mother."

"I don't think I feel comfortable with you being my psychiatrist anymore. You're a failure as a mother, letting your daughter have bastard children in a French convent. What would Miss Manners say?"

_Katie needed to curtsey when it was over? _

"I always knew you'd turn out just like Emily."

Wasn't that a compliment? "Thank you." She pulled a pair of oversized pink-framed Gucci sunglasses out of her clutch and slipped them on, playing the part of cokehead heiress oh so perfectly.

Daddy's money really was, like, the best thing ever.

* * *

You know that cliché, makes you want to throw up from pure lameness saying, your eyes are the windows to your soul?

Well, if you were soulless, did that apply?

This wasn't to say that Rory Gilmore didn't have feelings. As we saw, she expressed a lot of feelings in that elevator of sin with Jess. And she probably felt something at some point in her life before she decided the only way to solve her problems was to strangle her ex-best friend while looking like a fucking rock star.

Rory was sure E was sharing her sunflower comforter with Logan at this very moment, giving him some African strand of syphilis.

How long did you get in jail for a crime of passion anyways? Especially if the bitch deserved it. And sleeping with your best friend's sort of boyfriend qualified you as deserving to die during sex.

Unfortunately or fortunately, depending on how you felt about murder, Rory hadn't brought a gun. You couldn't call this move premeditated. She'd blacked out at some point (maybe from going around 90 on curvy roads) and found herself at E's mansion she shared with her maid/nanny/coke dealer.

The tricky part of this plan to strangle her ex-best friend to death, because she stole her panties, let Charleston touch her panties, which had somehow in her mind caused her to kiss Satan in a Calvin Klein underwear ad body, was that she didn't know how to get into her room.

_When did the front door go out of style? It was safe as long as you hadn't just banged some fat, pasty alcoholic's bored, tight assed wife. _

She decided she'd just march her way up to E's room. Who would mess with her when they saw her chapped lips, bare feet and soulless stare?

And by the time the cops arrived, E would be floating in the pool.

* * *

The sounds that were being echoed into the halls of E's mansion from her room rivaled the noises Rory probably made during her almost sexual encounter with Logan today.

She recognized that over-the-top, had acted out how Marilyn Monroe probably sounded when she came way too many times, moan that escaped E's lips.

Faking an orgasm was one of the three things E did better than anyone else in the world.

But the muffled crying was a bit alarming, one, because it was definitely coming from a boy and two, it definitely wasn't Logan.

It wouldn't shock her if E were taking advantage of some semi-attractive freshman that had accidentally told her she was pretty when she was extremely horny.

Which was always since Jess stopped pity fucking her.

She padded her way into E's bedroom and when she got a glimpse of whom E was faking for, wished she'd just waited for them to finish.

E was screwing Dean or Bleam or whatever his stupid name was. Mademoiselle Coco would be tres, tres desolee that she didn't get little floppy haired boy's jolly green giant inside her first.

Immediately, E sensed something evil was in the room, and by evil, she meant someone wasn't wearing any lipstick. That was only sexy when your lips were chapped from spending a whole day in bed with some Lord with a sexy accent.

_Did kissing Jess get Rory that get out of fashion jail free card? _

"Rory, my lipstick is in my Kate Spade bag. Please, put some on your lips." Aw, how sweet. Even though Rory was going to kill her, she wanted her to look her best while doing it.

"I'll pass. I'm not a fan of the shade whore."

Um, Guerlain's KissKiss Diamonds lipstick, E's favorite, came in more than just one shade! And unless she was a special whore, she couldn't spend 62,00 dollars on something that would wipe off every time a car pulled up to her corner.

E sat up, pushing floppy haired boy to the floor. She didn't care that her 32 C's were bouncing around. If you hadn't guessed, modesty wasn't that important to E.

"Um, this was sweaty and hot, Deanie Boy, but I've got better things to do and I don't have the time to wait to see if you can make me come before the sun goes down."

She had better things to do, like whoever would be joining her in the hot tub that night.

He was too busy crawling around on the floor looking for his _Iron Man_ t-shirt and Puma pants to form a response. And his jolly green giant was getting a bit out of hand with the presence of Rory.

Ah, we all knew zombie-hunting boy had a thing for Snow White. Poor E. No one really liked Sleeping Beauty. But she was a whore, so...

E stuck a French cigarette in the side of her mouth, looking a bit like James Dean, if he were alive and had a rack. She turned her attention to Rory and her Gucci framed face. "So, come for my sloppy seconds?"

"I think you're confused. You're the one who always wants what you can't have."

God, these kids and their soon to be incestuous ways. What was going to happen when they got bored with fucking each other?

No one pull a Gellar!

Dean or Bleam or something like that, pulled his _Iron Man_ shirt over his head, trying to think of some great parting line. "You know _Iron Man_ 2 is going to come out in 2010 and people are already buying tickets in advance. Would you, maybe, I don't know, like to go with me? My mom ordered an extra costume hoping I'd have a girlfriend by then and after today, I don't know."

How sweet in a pathetic, never going to happen, sort of way.

And E and girlfriend should never be two things that occupy the same thought. If Jess had a wandering penis, she had a runaway vagina.

She puffed out a perfect smoke ring, deciding how to explain to this poor sap that she didn't do any boy twice unless he had an accent or was currently high school sweethearts with her ex-best friend.

"She was horny and you were unfortunately there. Go get tested and hope you didn't accidentally knock her up." Insult or not, how sweet of Rory to get rid of a guy for E. This almost felt like old times. Just add a few cops and a lot of tequila and it'd be May 2006 all over again.

When Dean didn't budge, Rory wondered if E had just slept with one of the kids from the slow class. She'd heard stories about Dean talking to himself and some people said he had some weird superhero form of tourettes where he tried to fly, while cursing, but would E sink that low?

Rory might call her a dumb fuck, but she shouldn't fuck Chilton's Forrest Gump.

E rolled her eyes. Why did she always get stuck with the losers who were tragically bad in bed?

_Because at seventeen you run out of anyone with a bit of experience who has hit puberty by doing everything with a dick._

"Bye Bleam," she waved, hoping he'd get it.

"Oh you want me to…"

"Go? Yes."

She was sure he would start crying as soon as he realized he had to walk home but she didn't care. Rory was here. It was time to play.

With that unsatisfying distraction out of her way, she got out of bed to grab her Betsey Johnson black satin chemise.

Thank god. Rory couldn't strangle her if her boobs were flopping around.

She turned around, her cigarette dangling out of the side of her mouth. "God, that was such a disappointment. That teaches me to not pity fuck anymore."

"You're more experienced than anyone at Chilton. Maybe you should just start fucking yourself."

"Oh but that'd be so boring. Virgins can be fun. That's why Jess won't leave you alone."

"Does it make you jealous that Jess would rather sleep with me than you?"

E choked on her laughter, taking a few steps closer to Rory. "Jess isn't that fantastic in bed. Have fun trying to figure out if he is inside you or not."

"Oh my god, you're really jealous? You just can't stand it that I get everything you ever wanted."

"You're right. I wish a creep like Tristan cuddled with my panties every night."

"You didn't seem to blink an eye when you bedded him."

"That was before he went insane. Hey, I've got an idea. You two should put the past behind you and start going at it like bunny rabbits. He'd probably be able to satisfy you, since you're now a head case."

"You're one to talk. You just did zombie-hunting boy."

"He did my math homework for me. I had to repay him somehow." She blew a puff of smoke into Rory's face. "I have a question."

"This should be fascinating."

"Why can't you get Logan into bed? Is it because you're pretending to be the Virgin Mary that we all know you aren't or is it because deep down inside, you want Jess to do your deflowering?"

"I can't believe we were ever friends."

"Believe me, I'm not proud that I used to call a psychotic, sexually repressed troll my best friend." She stopped, moving so close to Rory that if those lesbian rumors had any truth to them, they could totally be doing it. "But there was one advantage to being friends with you."

"What?"

"Logan was much easier to get into bed."

Rory launched herself on top of E, sending both to the ground.

Rory wasn't athletic and only found herself breathing hard after having someone's tongue shoved down her throat or during a Stella McCartney trunk sale.

She got enough endorphins from ruining people's lives and eating Swiss chocolates. And when your body ran on ninety percent caffeine, exercise made your heart try to break out of your chest.

But if Quentin Tarantino were filming this, you'd never guess that Rory hadn't spent six months learning how to fight. She currently had E pined to the ground, holding her wrist so tightly that her nails were leaving marks all over E's golden skin.

E had about twenty pound and six inches on Rory's tiny frame, but it didn't seem to matter.

Rory fought dirty. She wasn't above ripping out E's golden locks.

"Rory, you're insane! Get off of me!" She tried to squirm her way out of Rory's clutches, but that just got her a palm across the face.

"You slapped me!"

"You deserved it!"

That rip, that was Rory ripping out some of E's strawberry scented hair. "You bitch! You don't rip out someone's hair!"

Had E never been a part of a catfight? Girls ripped, screamed and bit, and then hugged it out.

Except, unless Jesus himself forced these two to kiss and make up, there wouldn't be any hugging whenever this mess of claws and hair ended.

E bent her knees, sending Rory tumbling backwards. Her head bounced off of E's coffee table, shattering the edge.

"That table was a gift from Mr. Oscar De La Renta himself!"

"Shame he wasted a gift on you when everyone knows you give it away for free. What, was he trying to marry off his nephew? I heard he was a eunuch."

"Wouldn't a man with no penis be right up your alley?" Before Rory could answer, a vase slammed into her head. "That was a gift from Donatella. I never really liked it that much."

Currently, Rory was slumped against the wall, glass shards surrounding her feet.

You didn't rip out E's insured hair and expect to get away with it, did you Rory?

Superman himself must have given Rory a little boost, because even after shattering a table and a vase with her head, she was up again, marching her way toward E. And this time she had a little help in her hand called a wine bottle.

That was why you shouldn't keep alcohol in your room, you know, in case of crazy catfights with heavily medicated virgins.

E tried to back away, but there was nowhere to go. Her knees hit her bed at the exact moment merlot went dripping down her face.

At first, she hadn't felt the glass bottle shatter across the back of her head, but that burning sensation of wine mixing with open wounds could not be ignored for long.

Nor could she miss the blood and merlot staining her comforter.

She laid her head back against her pillow, her breathing slow and raspy.

For a moment, Rory felt a pang of guilt. But that quickly vanished when she found herself crushing a pillow into E's face.

Whoa, whoa, whoa! She wouldn't kill her, would she?

E's feet slammed into Rory's face, sending the pillow flying one way and Rory's little body into E's bookshelf.

"See Rory, sex is good for something. If I wasn't that flexible, I'd be dead. Sex saved my life." She stood up, taking a few lazy steps toward Rory. "I'm shocked you tried to kill me."

"All is fair in love and war."

"I underestimated you. I owe you an apology."

"I would apologize," Rory stopped, sweeping her legs behind E, all six feet of her sent crashing onto the floor, "but I'm not sorry."

Rory sat still for a moment, making sure E didn't start coughing up blood or something tragic like that where she'd be forced to save her life. When E just laid there, she figured she'd just been knocked unconscious.

Being hit over the head with a wine bottled tended to have that effect.

She noticed her French lace top was torn and covered in someone's blood. Her hands were riddled with cuts and her favorite skirt had been stained with merlot.

She stole a pack of cigarettes. E owed her that much. She really liked that skirt.

Surveying the damage of the room, she figured E's nanny was used to cleaning up messes like this when E either went wild on coke and sedatives or had that evil, evil boy over with the accent and prison record over.

E's diary entries were very detailed. Rory knew he didn't play nice, which kind of turned her on. If only he hadn't occupied E's vagina with his dick. They could have really had something.

Oh well.

* * *

Jess had found E in a lot of weird positions, some involving him without pants, others involving her ODing in his pool, but finding her in a puddle of blood and merlot might have been the oddest.

Especially since his current conquest was the one who had rolled around on the floor with her, until she passed out, he assumed.

"I didn't know Rory liked it rough with everyone. I thought I was special," he pouted, even though Rory's sadistic tendencies were hot, period.

E tried to stand, but her legs were a bit wobbly from deciding to go all _Kill Bill_ with Rory Gilmore. "If cared about you in anyway, I'd tell you not to fuck her. Imagine what she is going to do to you when she finds out it was all a game."

Run him over with her BMW. Shoot him in the face. Attach dynamite to him while he was sleeping and watch him go boom.

"Who says she has to find out?" he asked. He thought he could deflower her ass and then just not cuddle with her and that would be her punishment.

_Because spooning was so important to bitches. _

"Um, dipshit, that is sort of the point."

"I thought the point was for me to deflower her before Logan."

"Which will equate to social destruction."

"I hear it's quite a big deal to fuck me."

"Yeah, if you've never seen a dick before." Or were used to Logan's dick.

"I kissed her," he blurted out. What was next? Throwing pebbles at Rory's window and reciting some Shakespeare? Love was so unattractive and pathetic.

"When? Just now? She tried to kill me and you kissed her?" Maybe it was a celebratory kiss. No one liked little trick ass hoes, as we've learned from the poets of our generation: rappers.

"Before she came here and kicked your ass. In an elevator." With the candlestick? What was this, Clue: How To Do Rory Gilmore, style?

"Did you _just_ kiss her? "

He didn't like her pressuring him to seal the deal. If she wanted it done so badly, she could hike up her skirt and do her herself. "I don't know why I have to report to you."

"Because I own your ass at the moment. And if you don't make me happy, imagine what Lorelai will do to you when I tell her you took advantage of me, and forced yourself on her poor, innocent, daughter?" Forget Lorelai. Imagine what Emily would do. She didn't want any brown haired grandchildren.

His eyes went cold. "Don't try to cross me, sweetheart. I can turn this thing on you whenever I want to. I'm the one in control."

"All you are is a dick. If you decide to develop some sort of feelings or conscience, I can get someone else to fuck her." Good luck with that. Most of the male population at Chilton feared her.

"Like who? Yourself? I don't think she's as into you as you are into her."

"What is that supposed to mean?"

"You're obsessed with her." Uh oh.

"Go away. I have better things to do than talk about your theory on how I really want to sleep with Rory." She tossed what was left of the wine bottle at his face, barely missing his beautiful self.

_Thank god she missed. The world couldn't lose that kind of perfection._

He smirked because he knew she kind of did want Rory in a way that Republicans didn't like. "Aw, don't be like that."

"Don't come back here until Gilmore is too sore to walk."

Man, she didn't just want him to fuck her. She wanted him to channel his inner Sting.

"So now you want me to beat the shit out of her?"

She didn't answer, too mad that her Oscar De La Renta gown for her debut into society was ruined.

You normally didn't feel like bantering when a ten thousand dollar dress was ripped, stained and missing all the tulle.

* * *

He'd found a lot of girls in his room in various states of undress. His favorite was Veronica. She was European. She didn't believe in wearing a bra. Or a shirt, most of the time.

He meant his old favorite. Who he found in his room at this very moment was going to be way more fun than Veronica and her always-hard nipples or Louise with her inability to never get off her knees.

Even if she took a wine bottle to his head as well, it'd be worth it. Because he kind of sort of wanted her in more than just a 'you're hired to do her' way.

She hadn't changed, still wearing that little see through Zac Posen top or what was left of it. She looked awful and perfect at the same time.

_That was the insanely rich for you. They could get away with almost anything. _

He took off his leather jacket, making him look less like Marlon Brando and more like a bad, bad schoolboy.

Maybe Rory was here to spank him. Let's hope she kept a ruler in her purse.

He took a step toward his bed. Who would of thought it would have been this easy to get her in his bed? "How'd you get in my room?"

"Your nanny has always liked me better than you." Or maybe it was the fact that she looked like she was being chased by flesh eating zombies or an ax murderer. Maria would be deported if she let Miss Hayden-Gilmore be cut into little pieces by Dean or Bleam or something like that and his crazy bother.

"You didn't screw her when you were sixteen." That's right; Jess did his nanny. But he couldn't help himself. He was just taking after daddy.

The closer he moved toward her, the more aware she became of her position. She was on his bed. He could see _everything. _Why had she come here, like this? Why was she waiting for him, on his bed? She knew he expected something to happen that would force him to wash his sheets. "I don't know why I'm here."

"I can't answer that for you." He definitely hadn't lured her here. He wasn't Dracula.

_And this wasn't a Dateline special in the making. _

"I just showed up." Meaning she walked up to the front door, then went back to her car a thousand times before she realized how much she looked like Carrie's long lost twin and opted to go inside. At least Maria would make her a martini.

He smirked. Of course he didn't believe her. "Really?"

"Yeah." She stopped. "No, that's a lie. I wanted, no, I had to know something." The quickest way to Jess' penis was to ask. Wait, that wasn't the question? Oops.

"Yes, I have condoms. In the night stand."

She blushed. He loved it when she did that. It was so innocent and pure. And that purity was something he would love nothing more than to tarnish. "Shut up. If you don't shut up I'm going to hate you even more than I already do."

"I'm glad to know I haven't reached the highest level of loathing."

She sighed. "Did you mean what you said?"

He truly had no idea what she was talking about. "When?'

She bit her lip. He was going to make her say it, wasn't he? That loathsome imbecile with his perfect cheekbones. "The other day."

"Which day are we speaking of?" There were seven days in a week, and you two had been spending a lot of time together. Can't blame the boy for needing a bit more reference.

"Are you really in love with me?" she blurted out. Most girls would have been busy planning their wedding at the Plaza but Rory was too busy trying to avoid one of those lame, tragic love stories. Romeo and Juliet were retarded.

He smirked. "Who told you that?"

Her face fell for a moment. "I heard it." While you were crouched in the corner waiting to stab E in the back with your...sandal. Yeah, best not to repeat that brilliant plan to anyone.

"You were eavesdropping on me?"

"Does it matter? You said it."

"Yeah, I did," he admitted like it wasn't a big freaking deal even though he'd just told her like, five minutes prior to that exchange with E, he had never been in love in all his years of whoring.

"So did you mean it?" Casanova and Holly Golightly. It could work.

"Yeah."

She stood up, making her way toward him. "You stupid fuck!"

She hit him a few times with her clutch, then ran out of his room, leaving her gin martini. And her pride.

He was supposed to say no. He was supposed to try to get up her skirt. But he just stood there, looking perfect, and said 'yeah.'

'Yeah' was such a lame response, anyways. She couldn't kiss boys who said 'yeah.'

But why, why was it that even though she loathed him and thought he was a despicable human being, she felt a rush of something that might be butterflies when he said 'yeah'?

Well, those butterflies needed to die.

Die, die, die love butterflies. Rory had no use for you.

* * *

**Ending Author's Note**: So catfights. I dig em. They are demeaning to the female race, yet awesome at the same time. And I figured as long as I didn't have the HBC cheering them on, it wasn't too crossing the line into _Girls Gone Wil__d! _Over-the-top? Totally. But that is why this story is so much fun.

By the by, I'm looking for an idea partner/beta for the fall. There is more on it in my profile. If you want to apply (there will be an intensive screening process akin to getting hired at Starbucks) go to my profile page and either hit send message or email. Both go to the same place cause I'm a one stop candy shop.

**Reviewers**: Maybe one day our love will be recognized as a real, constitutional thing outside of California. Or maybe we'll just be forced to continue our tryst through reviews. Damn the government!


	6. Check This Hand, Cause I'm Marvelous

Chapter 6: Check This Hand, Cause I'm Marvelous

**Author's Note**: Fuck, shit, damn, hell, it has been a long fucking time since I've been around these parts. I think my fan fiction virginity grew back in that time. My extended absence can only be blamed on alcohol. I've been drunk for almost two years. I'm that badass. Hemingway actually sent me a letter, from the grave, commending me on my ability to be more fucked up than Zelda Fitzgerald back in their days when they kicked it in Paris. Ah, just kidding! Writing fan fiction just seems lame now. I know, blasphemy! It's like I'm dick slapping all of you readers by saying that. And I'm sorry. But this just isn't my format anymore. I still write about fucked up people, just in a less Gossip Girl, more realist, life sucks but we don't all know Oscar De La Renta, way. But, I've had this chapter hidden away for awhile, working on it de temps en temps and tonight, I was like, fuck it, I'm going to post this teaser. And really, that's what this chapter is. It wraps up nothing. I end it on a cliffhanger. And being a total whore, I made this chapter quite a bit shorter than others. But while I was editing this, I chuckled quite a bit. Yes, I'm into myself enough to admit I entertained myself. So after writing my autobiography of an author's note, I don't know if I should ask for a welcome back party or for you to accept my apology for being such a terrible fan fiction whore. Tell me in your comments what you think.

**Disclaimer**: I have a complicated relationship with Lady Gaga (God, wouldn't that be an awesome facebook thing? Someone join facebook as Lady Gaga, friend me and let's get complicated together). I don't really like her but I understand her appeal and think she's sort of a genius. I hate that she is a genius but she's a genius for this time. But in ten years, she's going to suck. She's going to suck so hard that when her song comes on, you'll remember all those times you loved it and then remember you had to be drunk to love Lady Gaga, and then you'll get drunk. But this lyric is too awesome to not use as a title for this materialistic story. So yeah. If you moved to the mountains and grew a beard and wrote folk songs about your latest break up, this title comes from Poker Face. Check out Jude Law's dramatic reading of the lyrics. It makes my panties drop.

And now, on to the story.

* * *

In a world where you had champagne for breakfast and wore True Religion jeans, you became a woman not when you were, finally, properly fucked (you're allowed to discount that disappointing, awkward, unnaturally tangled first time) but when you were presented into society in that tragically ordinary Oscar De La Renta white gown.

Crème wasn't allowed. Off-white was for those horrendous knock offs you'd find under the pier in Jersey. If you wanted to be a Hartford debutante, it required an Oscar original, white gloves and a Prince Charming to waltz with.

_And fuck in the suite your parents owned upstairs. _

Rory should have been focused on getting her Oscar Grecian Gown fitted by Mr. De La Renta himself. She shouldn't have been wallowing in Mia Farrow's Black and White Oscar dress from Truman Capote's 1966 Black and White party, watching _My Fair Lady_.

One, you didn't wallow in a 3,000 dollar dress Mia Farrow wore to the Black and White ball, and two, you didn't wallow, especially when you had the most perfect dress sitting in your closet.

Tomorrow was supposed to be the happiest day of her life. She was finally becoming a debutante. Her boyfriend looked like Daniel Craig in a tux. She'd ruined E's dress. What was there to be sad about?

Oh yeah, kissing James Dean. The James Dean who maybe kind of sort of loved her, if you believed the words that exited his perfect lips.

Love was such a ridiculous, wasted emotion that only happened in Paris when you were drunk off the Eiffel Tower and a wine from Cotes-de-Bourg.

Rory hated Paris, thought Cotes-de-Bourg wine was a thing that only the country club crowd drank to wash down their Xanax and didn't want to fall in love. Or be in love.

She hated being around people who were in love. That was why she treated Logan like shit and vice versa.

_Take notes, Jess! _

Maybe she should just fuck the pool boy, Javier. She'd spent the summer lying by the pool in her Norma Kamali red bathing suit pretending to understand his adorable Spanish accent. They'd fooled around in the pool house the day after Rory found out about Logan's little private going away party for E. It was hot and all, but he drove a Volvo and went to community college, so no matter how hot it was when he taught her to tango, he wasn't Rory Gilmore worthy.

But, she was bored. Her Mia Farrow dress was better to look at than to wear, and all the tension Jess had built up in her was just begging to be put to good use.

And Javier looked really good with his shirt off.

It also helped that E had wanted him, and he'd said no to the toxic vagina and blonde hair. No! He was the only hot boy in Hartford who hadn't risked his life for a little pussy.

And did we mention he had a Spanish accent? And knew how to tango? And rolled his tongue in this oh so perfect way…

_Oh summer flings. So hot. So dirty. But so out of style in the fall. _

To fuck or not to fuck the Spanish pool boy, that was the question.

But before Rory had time to weigh the pros and cons of doing under water ballet with Javier (pros: he was hot. Con: he was poor. Ah, hot versus poor. It was like the historic battle of good versus evil, except superficial. And it brings to mind a certain Kanye West song, but it was important for your man to have money for all that work you were going to need) she heard a knock on her door.

"Go away." Bored with her pathetic state, she paused _My Fair Lady_.

As much as she loved Audrey Hepburn, sometimes, she wished she'd shut the fuck up. Who would ever be happy enough to dance all night? Happiness was ridiculously large chocolate covered strawberries and a warm gun.

_Um, even robots fall in love, Rory. _

"Miss Rory…" Greta hid herself behind the door, just in case Rory decided to throw that vase of roses Logan had sent her. To apologize. For not fucking her.

Rory hated roses.

"I told you not to bother me while I was wallowing, Greta." Oh to be young and full of self-pity.

"But Miss Rory, it is Master Jess. He says it is urgent." As in his pants are constricting his ability to do anything and he needs a bit of assistance, urgent?

"Tell him to fuck off and die." There was one of those phrases you wished you could find on a Hallmark card.

"I'd rather not."

"Greta, you let him in the house?" Well, it'd be rude to not invite your Romeo in for tea, Rory!

"I'll take it from here, Greta." Jess gave Greta that disturbing, 'I'm about to deflower your dear, sweet, Rory' smirk of his.

"I'm telling my mother and she will have you deported back to Russia!" Bad move, Gilmore. Hell hath no fury like a Russian maid scorned. Your cashmere sweaters will never be soft again. And lock your jewelry case. Russians love a side of diamonds with their vodka.

When Jess locked the door, Rory lost it. She remembered that dream she had the other night. They were in the library. She was in a green dress. Yes, she had the obligatory _Atonement_ fantasy every girl in the world was having at this very moment. Mock her later for her lack of originality. But right now all she wanted to do was grab him and ki…kill the motherfucker.

"No, Greta, I didn't mean it. Please, come back. Please."

He somehow, in the span of a second, was millimeters from her lips, leaning over her in his disgusting, rapist sort of way. "You don't trust me?" he breathed.

She pushed him away. She was Rory Hayden Gilmore. She was not going to let Jess Mariano get under her skin. Or her La Perla underwear. "I don't trust your dick."

"I think it is more likely you'll violate me with your tongue."

Her eyes rolled into the back of her head. But not for the reason Jess was hoping. "You wish."

He slid his hands into his pockets and leaned against the wall. If he lit a cigarette, he'd look just like Marlon Brando. And then, Rory's panties would be forced to come off. "I have a little video from our tryst in the elevator to prove it."

She set up, tucking her hair behind her ears. All of sudden, she had sprung into Emily Gilmore mode. Mentally, she was already planning where to dump his body. "Are you blackmailing me?"

"No. I just wanted it as a memento." Jess eyed her outfit but not in his normal violating sort of way. "You look ridiculous."

"And you say you love me." Actually, he said 'yeah.' It was too soon to say 'I love you.' There hadn't been enough suffering. All seventeen-year-olds had to pretend to be tragic at some point in their courtship. Rory and Jess were no different, if you forgot that they partied in the Hamptons and ruined people's lives to burn calories.

"It was a slip of the tongue."

"Oh." Is that disappointment we heard in Miss Gilmore's voice? Was she in love with Jess Mariano, the same boy she swore to hate on countless occasions? It couldn't be, could it?

"You didn't really think I loved you, did I?"

Any sign of disappointment was gone. Any sign of anything was gone, actually. She really was ready to take over Emily's throne as the ice queen of Hartford. "No."

"Because people like us are incapable of love."

"Stop comparing us."

He lit a cigarette, because he knew she'd either rip his cardigan off or throw her vase of roses at him. Either way, he came out on top (even though he preferred the idea of her straddling him). "But I'm quite a fan of the idea of fucking you. In your bed, by the way."

"Why are you here?"

"I thought I made that clear."

"I'm not fucking you in my bed. My sheets are far too expensive." Jess' dick was as lethal as E's vagina. A Burberry scarf you found at Goodwill might be the only thing worthy of his dick, so either buy your Egyptian cotton from Target or Rory would die tighter than Queen Elizabeth.

Come on, we all know if Jess doesn't deflower her, no one will. It takes a King to dethrone a Queen. The Court Jester just won't do.

It.

As we've seen.

"Then how about against the wall?" Poor, poor Greta. Someone needed to warn her of the fluids she would come in contact with next time she cleaned Miss Rory's room.

She bit her tongue. He did that to her. He made her forget that she'd washed her hair. He made her lose the ability to eat (even though it went against Emily's debutante diet to eat anything but almonds and Evian). He made her wallow. Wallowing led to mass consumption of Chunky Monkey, which totally went against the requirements of wearing an Oscar De La Renta dress.

Mia Farrow weighed seventy-pounds. Rory had a lot of unnecessary weight that no one appreciated. She might be forced to break a rib or two to fit into her dress. Whatever. She was born to suffer for fashion.

Jess made her hate herself, basically. "Did you come here for any reason besides being a complete asshole?"

His pants felt a bit tighter than they had this morning. It was becoming increasingly hard for him to control his need to fuck her. "Is Logan your escort for your little coming out into society?"

"I didn't know you were capable of being straight to the point."

"When I want someone…" He took a step, his eyes focused on her collarbones. He wanted to run his tongue along…well really, anywhere on her body. He wasn't picky.

She put up her hand. This was not happening. This could not happen. "Don't finish that sentence. I'm not going to ask you to be my escort."

"Why not?"

"The short or the long version? Simply, you disgust me. And I doubt you'll look half as good as Logan will in a tux."

James Dean versus Daniel Craig. Oh, we can't choose. Our vaginas won't let us! How can we expect Rory to decide?

"You evaded my question."

Her face fell. She couldn't convince him, her supposed boyfriend, to fuck her. Why would she expect him to put on white gloves for her? Those white gloves were more than just an overly gay gesture. With those gloves, he was promising Tiffany's, 2.5 kids, a golden retriever, and ten years of wedded bliss, if you forgot that one of them would become an alcoholic, he'd keep a mistress on the side that enjoyed dick more than Chanel (Louise, maybe?) and Rory would medicate in the best way possible: Jess Mariano's dick. "That's because I don't know."

"Then let me take you. As friends."

"Friends?" Let us echo her statement: friends? Friends don't let friends take each other's clothes off until they've emptied a bottle of Grey Goose.

"Friends."

"You'd have my dress off before we even made it down the steps."

Her coming out would definitely be memorable. And chilly.

"Only if you helped me with the first few buttons."

"Why are you being nice?' She considered this nice? Oh, we forgot: she hates nice people.

"Call it an apology for kissing you in the elevator. And for saying 'yeah' to your question in my bedroom." He brushed his needed-to-be-cut-because-he-looked-like-a-cross-between-Wolverine-and-an-emo-kid hair out of his face. If he wasn't so him he'd be disqualified as a possible escort for the hair alone.

But he smelled like London and evil, Rory's favorite scent.

She perked up. Jess Mariano did not apologize. Ever. "There would be rules."

"Such as?"

"No touching. No getting me drunk. No taking me back to your father's suite. And no fucking."

It'd be clichéd to be deflowered after you came out, anyway. Rory Gilmore was many things but she wasn't a cliché.

"Why do you assume I have control over the last thing?"

"I don't loathe you entirely but you're Jess Mariano. Date rape seems like something you'd enjoy."

"Now you hurt my feelings."

"You don't have feelings."

"And neither do you."

"So maybe we're meant to be best friends."

"I wouldn't go that far. If you're my best friend, I can't think about you when I…" His eyes traveled to her perfectly perfect cleavage. It was just sitting there, waiting for someone.

_But who? _

"If we're friends you can't do that. So stop it. I'm not letting you escort me if you say things like that." Because then she'll do things, like him.

"I feel like we should shake on this." Jess Mariano sure did like deals that involved Rory Gilmore and fucking.

She scrunched up her face like she'd just seen her mother wearing last year's Diane Von Furstenberg wrap dress. Perish the thought of wearing something from the 09 collection! "I'd rather not."

"Why? Afraid you might jump me in my school boy uniform?"

"No. I just don't know who you've had that hand in today." She gave him that little smile of hers that said 'get the fuck out.'

She had such polite facial expressions.

But again, friends? Seriously? This had to be the dumbest idea we've ever heard. You can't tongue fuck in an elevator one day and then have slumber parties, that involve both parties being fully clothed, the next.

And what about Javier?

* * *

Riddle me this: what's blonde, slutty and in need of being vaccinated?

Given up? Want another hint?

Oh I'll stop being such a tease and get to the good stuff.

This blow up doll was currently having tea with Hartford's favorite ice queen.

What could these two bitches have to discuss besides New York Fashion week and the fit of E's Oscar original?

Oh yes, we forgot about the person they share, who was currently ringing her grandmother's doorbell: Miss Rory.

This is far too delicious to even comprehend.

* * *

Rory wasn't one to wait for the maids. She preferred barging in, a la Miranda Priestley, and leaving her Lorick cape draped over a piece of furniture, just to piss her grandmother off.

If she were in a really good mood, she'd pull out her pack of cigarettes during tea.

"Miss Rory! Miss Rory!" Ugh. Rory hated her grandmother's incompetent (weren't they all? Didn't the word maid reek of incompetence?) Swedish maid. She thought she would be better suited as a milkmaid.

Or playing a milkmaid for an escort service.

Rory glanced over the shoulder of her Nanette Lepore Ingénue strapless dress. It was just something she'd thrown on with a pair of leggings.

_Thank god she wasn't still walking around in that Mia Farrow gown all zombie!Rory like. Emily would have her committed. _

"Heidi, stop following me!"

"But Miss Rory, your grandmother…"

"Invited me over for tea."

"But an unexpected visitor stopped by and she told me to…"

She stopped, almost falling out of her Pedro Garcia Noa pumps. Damn her personal shopper. She always bought a size too big. Oh well. She'd be fired later. "Name one person that is more important to my grandmother than me."

"Oh Miss Rory, this person isn't more important, per say. It's just, we all know…"

"Is Jess Mariano having tea with my grandmother?"

"Certainly not. Mrs. Gilmore finds him to be a vile human being!"

"Grandma always had terrible taste in men," she muttered, without realizing what she'd just admitted.

"What was that, Miss Rory?"

"Nothing. Absolutely nothing. Now why can't I go see my grandmother, Heidi?"

"It's Miss Rigby."

"My grandmother would never have tea with someone whose vagina is used as a playground by every man in Hartford."

"She just showed up. She was not invited."

"Obviously."

"Do you need a moment?"

"Yes!" She screeched, slamming her heels into the mahogany.

She just needed a moment. That was all. She certainly wasn't going to have a meltdown.

It was not like a little freak out wasn't normal for society girls. It's hard to juggle looking fabulous, kissing the right boy and not falling in love with narcissistic assholes that are completely wrong for you.

The right accessory for Rory Gilmore wasn't the boy who complimented her Fendi bag, unfortunately. The longer she denied it, the more therapy she was going to need.

She rummaged through her grandmother's medicine cabinet. She was Hartford's Judy Garland. There had to be an upper somewhere in her stash.

_Society kids and their need to mix prescription drugs and cocaine. Tsk tsk. _

She popped a Quaalude. It'd have to do.

"You don't love Jess Mariano," she said into the mirror. Who was she trying to convince? "You can't love Jess Mariano."

* * *

E placed her hand on top of Emily's. "I've always thought of you as the grandmother I never had. You were so good to me after Pop-Pop died."

"Your Pop-Pop was…"

"A terrible man who drank too much and hated me for not being a boy. He also didn't understand the color pink."

"Excuse me?"

"He said it was an extravagant waste of coloring that reminded him of Pepto-Bismol. I think it went along with his distaste for all things feminine. My therapist said he was a repressed transsexual."

"Oh my."

"But never mind that. I didn't come here to share tea and gossip about Mrs. Mariano."

"Such a whore."

"Just like her son."

"Oh you're such a glorious bitch!"

"Coming from you, that means so much," she paused. Another Oscar worthy performance, perhaps? Watch out, Kate Winslet! "You're everything I aspire to be."

"Stop!"

"I'm serious. You're the epitome of what a Hartford woman should be. I've always envied Rory for having you as a grandmother."

"She doesn't seem to appreciate me very much."

"Well, she has been hanging out with some unsavory characters as of late."

"Who?"

"I hate to be a little snitch…"

"Her mother ended up pregnant at sixteen because of that awful Hayden boy! I must know!"

"It's Jess Mariano. Apparently, Headmaster Charleston found them fornicating in the library."

"What!" Those Gilmore women sure do know how to screech.

"Oh dear, have I said too much? I've said too much. I better go. Thank you for the tea, Emily. And when you see Rory, don't be too critical. There was a time when I was swayed by the Mariano charm."

"This can't be true. She's with Logan. She is going to marry Logan. There must be some kind of mistake."

"Charleston found her underwear in a copy of _Anna Karenina_. No one else has read that book at Chilton, aside from Jess Mariano."

"This all makes sense now. At Lorelai's party, the sloth was lurking. And then Rory rushed to her room in tears. Oh god, what if she's pregnant?"

"At least their children will be literate. And there are excellent places you can send her in France when she starts to show."

"Marc Jacobs doesn't make maternity clothes!"

"Maybe he'll make an exception for the Gilmore's."

"I need a gin and tonic. Heidi! Heidi!"

Fifteen seconds later, Heidi was on the patio with the drink in hand. Fifteen seconds was not acceptable when the crisis required alcohol.

"Heidi, I could have you deported."

"I'm a citizen, Mrs. Gilmore."

"It takes fifteen seconds to make a gin and tonic? Are you somewhat impaired and decided not to share that bit of information with your employer?"

"I've been practicing…"

"You pour as you move, Heidi! We've been over this. And stop slouching. I pay you to not slouch."

"Yes, Mrs. Gilmore."

"Stop standing there like a drooling fool and hand me my drink."

"Its just…may I speak with you in private?"

"Miss Rigby's breeding is far superior to yours. Didn't you grow up in a field playing with bunnies and braiding hair?"

"Your granddaughter is here."

"Well send her out. Miss Rigby and her are the greatest of friends."

"I don't think…"

"I didn't hire you to think."

E knew she had three seconds before Rory appeared and threw a fit, wasting crumpets and tearing her Milly dress with the jam knife. It was time for E to disappear.

"Oh Emily, I'm afraid Rory and I had a falling out over her current lifestyle. I just can't be around people like that anymore. Mommy wouldn't approve. I think it would be best if you confronted her without me here. She might try to kill me."

"Don't be silly; Rory reminds everyone of Bambi." With fangs and heels and a penchant for being evil. That Bambi.

"Well then, we must think about the baby."

In one hand was a glass that had a splash of orange juice with half a bottle of Prosecco. In the other hand was a gun. No! We're just kidding. Rory wished she had a gun, but in the words of the queen "Tea wasn't meant to be a bloody affair!"

"Grandma, you didn't tell me you had invited E over for tea." It appeared Rory had opted to act like a lady. This was good. Her grandmother wouldn't approve of her depraved hedonism.

But let's be honest; didn't everyone in high society practice depraved hedonism? Wasn't it all about getting off, no matter what?

"Why do you insist on calling her by her first initial? Have I taught you nothing? Her name is Elizabeth."

"I never thought Elizabeth suited her that well. Far too virginal."

"Oh Rory, you always had your mother's wit."

"And you inherited your mother's ability to turn every man in Hartford into a blithering fool. Tell me, have you and your mother fucked the same man yet because that would just be too precious."

"Rory Hayden Gilmore! What has gotten into you?"

"Jess Mariano. You better get her checked out. Last I heard he has genital herpes. I hear he doesn't' tell girls unless it flares up."

Rory forced a smile. "Grandma, don't you think Heidi should see the whore out? It is our teatime. And don't you have a sex addiction recovery meeting to attend, E?"

"Don't throw stones, Gilmore. Isn't your mother a recovering alcoholic?"

"Only because of my father's need to give everything that walked by his limo a ride."

"This is highly inappropriate conversation, ladies."

E ignored Emily. "Like mother, like daughter."

"What's that supposed to mean?"

"You and your mother are unable to keep a man faithful. Wonder why that is? Emily has trained Richard like a Labrador."

Heidi rushed in with E's Michael Kors wool coat, throwing it over the blonde's face.

She saved her from being doused in peppermint tea and Prosecco, which was a shame, because everyone wanted to know if E would melt.

For some reason, Heidi liked Rory. Was it even possible to like a self made bitch that verbally assaulted anyone who couldn't pronounce Balenciaga correctly? Maybe Heidi and Rory could form a bond of master bitch and protégé!

* * *

"Grandma, how could you let her in the house?"

"I didn't know you two were no longer friends."

"It's all over the internet!"

"And what is this nonsense Elizabeth tells me about you and Jess Mariano fornicating in the library? And let me remind you, that is the library you begged your grandfather to pay for. Did he buy you a fornication library?"

For Jess Mariano, everything was made for fornication. When you took a tour of Chilton now, you had two options: the historical 'this school was founded in 1898 by a poor white man with a dream' route or the 'where Jess Mariano has fucked' edition. Both were equally educational. The only difference: it was recommended that you wear plastic gloves for the latter.

"She's delusional. All the coke she did is finally catching up with her."

"So you're not pregnant?"

"Child birth is vile."

And it leaves stretch marks! Ew! Bikini season was officially closed forever after you gave birth. There was also that nonsense about no cocktails for nine months.

"Because we'd pay to have you fixed."

"I'm not a poodle."

"Yes, but if you couldn't control yourself around that boy…"

"But you'd be fine if Logan impregnated me?"

"Since you'll be married at some point, it wouldn't be as upsetting."

It would upset evolution.

"I'm not marrying Logan!"

"Oh don't be ridiculous. Jess Mariano will inherit Jimmy's business when he dies and squander all the money on booze and women with questionable morals."

"Logan is no better."

"The Huntzberger name will do wonders for your social status, dear."

Emily couldn't let her granddaughter's brief fling with insanity make its debut into society tonight. She had kept Lorelai's alcoholism, brief stint in rehab when Rory was still shaking her Tiffany's silver rattle, and her own love of Vicodin away from those vultures. Her granddaughter would not ruin all of that damage control by being stupid like her mother was. And besides, she would lose that most coveted invite to the Huntzberger Christmas party if Rory started dating that Mariano boy, who Emily was sure had a strand of syphilis that would ravage her perfect, seventeen-year old body.

And the Mariano Christmas party consisted of Jess entertaining three foreign exchange sluts in the pool-house with the sounds of Bing Crosby and his dick. It was a very private affair that Rory would certainly not be attending. Ever.

"Social status? That's all I am to you? Social status?" Rory screeched.

"Rory, dear, you know how important it is to keep your name out of the papers in Hartford. Your mother doesn't understand how all this works. I'm merely protecting you," she reminded her.

"By forcing me to be with someone I don't love?"

Love was relative, no? Who really marries someone for love nowadays? Elizabeth Taylor should be our role model, not our 'don't turn out like her' example.

"You'll learn to love him."

"Before or after he cheats on me, again?" Rory became ice cold. "I'm not feeling like tea today, grandmother. I'll see you tonight at the coming out, I suppose." A wicked smile spread across her flawless face. "Jess Mariano has agreed to be my escort."

She didn't wait for Emily to have a classic Gilmore meltdown. She could hear her screaming for Richard, which meant in three seconds he would exit his office, scotch in hand, ready to do some sort of damage control.

Rory didn't care. Tonight was no longer her coming out. Tonight was all about ruining the Gilmore name. And if she had to fuck Jess Mariano to complete the destruction, oh fucking well.

* * *

Rory pulled out her phone. "I need your help, Mariano."

"I thought we promised to just be friends."

She rolled her eyes. "Not in that department. I've decided to take down the Gilmore's."

"You are a Gilmore."

"My grandmother sees me as a chess piece. I'm sick of being moved around a metaphorical board by her. My whole life was planned out for me before I even knew what Gucci was. Logan, Chilton, Yale. It was all the great Gilmore plan. And a few days ago, I was fine with that. I was fine with being a pawn. But not anymore. And I need your help."

"You know I'm always up for a good game of ruin your chances at a trust fund."

"That's why they call you the King."

"Actually, that's what I require girls to say when I make them come."

"Focus, Mariano. My grandmother hates you."

"It must run in the family."

She ignored him. "The Gilmore's worst fear is that I fall in love with you."

"I don't normally agree to plans that involve the word love…"

"Don't worry, Mariano. I'm not the kind of girl that falls in love."

"You finally admit it."

"Just act like the idea of us being together is not completely disturbing. Not that it isn't. Because it is. We would never work out."

"Why are you reminding me?"

"I just thought I should make it clear before we go through with this that this in no way opens the door for us to be a thing. I don't want to be a thing with you."

"And what makes you think I'm entertaining the idea of being a thing with you?"

"I don't think that. I just…"

"Maybe you're saying it for your benefit, Freckles."

"I know what I want."

"And what is that?"

"Not you."

He smirked. "And exactly how far do you want to take this charade?"

"How ever far it needs to go."

"No limits? No rules? Where is the fun in that?"

"This is your one chance to do whatever you want to me and you're complaining?"

"You know I like the chase."

"Well after tonight, you can continue to chase me."

"Oh Gilmore, you really know how to get a guy going." He paused. "I have one request for the night."

"What?"

"Don't wear anything under your Oscar dress."

"That's not ladylike," she teased.

"I'll have to teach you some manners then, I suppose. My limo in front of the Met at 8?"

"I'll bring the champagne."

"I'll bring my dick."

"Such a gentleman."

"I'm your Carey Grant. Stop denying it. When you touch yourself, who do you think about?"

"Hemingway." And with that literary jest, she hung up.

* * *

"Miss Rory, you look lovely."

Rory applied her strawberry lip-gloss. Jess' favorite. "Thank you, Greta." When Greta didn't immediately exit, Rory knew something was up. "What is it, Greta?"

"It's Mr. Jess. I know you find him to be vile and you're in love with Mr. Logan, but the way he looks at you, well, I think Mr. Jess is in love with you."

"The way he looks at me? What does that mean?"

"At your mother's party. He looked bored with everyone else in the room. But when you came his way, he lit up."

She didn't miss a beat. "That's called an erection."

"And I see it with you too, Miss Rory. You're different around him."

"Stop it, Greta."

"You shouldn't listen to your grandmother anymore. You don't want to end up like her."

"And my mother is so much better? All she has is her vodka to keep her happy."

"You could have Mr. Jess."

"I don't want him."

"It's weird, Miss Rory, to go around pretending you don't want the one person that makes you happy."

"He doesn't make me happy." When Greta didn't say anything, Rory lost it. "He doesn't! God Greta, you know nothing about this world or what it takes to be me. I have to be perfect every fucking day. My headband can never be askew. I have to be seen with the right people. Drink the right martini. Wear this year's Chanel. I don't have time to slum around with people like Jess Mariano. And even if I did love him, which I don't, he doesn't love me."

"How do you know?"

She wanted to cry. "He said so."

"Oh Miss Rory, he didn't mean it."

"Please, don't pity me, Greta. Now could you hand me my headband and leave me alone?"

She stared into the mirror, placing the Jennifer Behr Rosette headband she'd picked up on a whim from Saks on her head, a lavish accessory for her effortlessly pulled back locks. She looked perfect. Even her messy bun was the type of mess that seemed intentional. Her eyelashes were swept with two strokes of Dior.

"You are perfect," she said to no one. And then the tears started. But who were these tears for? The boy she didn't love?

"You are perfect and he doesn't want you." And in true Gilmore fashion, all emotion immediately disappeared. Tonight was her coming out. She could cry later. There was champagne to drink and crotches to grab.

* * *

"You look perfect." Of course she did. She was a Gilmore. You could throw her in a trash bag and she'd look marvelous. But having a hot boy compliment you was always nice.

Rory smiled. "I do believe that's the nicest thing you've ever said to me, Mariano."

"Did I not compliment your lips?" He moved closer to her in the limo, close enough to whisper in her ear. "They're my favorite thing about you." He ran his finger down her arm. "Correction: they're my favorite thing about you I've gotten to know, personally."

She scooted away from him. "You're drunk."

"Only a little."

She shook her head. "This isn't how this night was supposed to go."

He sighed. He was annoyed with this game, because in some weird, Jess Mariano logic, he thought he'd gotten the girl. "Let me guess. Logan was supposed to ride in on a white horse with a thousand yellow daises. And as you descended the stairs of the Gilmore mansion, Moon River begins to play."

"And instead I'm in the back of a limo with you."

"Dreams do come true," he smarted, moving away from her.

She looked at him. "Are you upset?"

"Why would I be upset that Gilmore wishes it was Logan in this limo and not me?"

"You don't even like me. You said earlier today you didn't love me."

"I don't."

"Then what's with the attitude?"

"I'm bored with this game. Are we going to fuck or not?"

"Is that the only reason you asked to be my escort?"

He took a sip of his scotch. "You're just like all the others."

"I thought…" she trailed off.

"That I cared about you? That after tonight things between us would be different? You told me on the phone we would never become a thing. You said it, Gilmore."

"I don't know what's going on."

"Fuck if I understand this situation."

"Why are we acting like this? This isn't us. We like games. We like ruining people's lives. We care about no one but ourselves."

"Then fuck me."

"What?"

"I care about myself, which means I care about getting laid. Fuck me."

"You can't be serious."

"Did you think your first time was going to be special? That there would be candles and fireworks and some weepy love song playing right when you were about to cum? Did you think it'd be with someone you loved?"

"Why are you doing this?"

"What?"

"Acting this way."

"Because I can't do this anymore."

"Do what?"

"Pretend."

"What are you talking about?"

"I don't know."

"No! You don't get to do that. Say it." She paused. "No, don't say it. Just kiss me."

"What?"

"Kiss me. I know you want to. Just kiss me."

Jess stared at her. He moved closer and brushed his lips against hers. It was gentle, unlike their first kiss.

"I didn't wear anything under Oscar," she whispered as he pulled away.

"Rory, do you know what you're doing?"

"I'm tired of being a virgin."

"I'm tired of you being a virgin."

"Let's work on fixing that problem, then, shall we?"

"As you wish."

* * *

Her eyes flew open the instant all the alcohol left her system. She looked around. There was her dress. There was her headband.

But where the fuck was she? She needed to google map herself. Or find her phone and check it. She could always rely on drunken text messages to help her figure out what the fuck happened and where she should tell Oscar, her limo driver, not the designer, to pick her up.

But then she saw something move in the corner. And that something was Jess Mariano.

"Morning, love."

"No. No. No. No. No," she kept repeating.

"My god, why are you talking?"

"This did not happen. No. No!"

He smiled. "What do you think happened?"

"I don't know but I feel…"

"Sore? Properly fucked?"

"Like I'm going to need to get vaccinated. Oh my god, did we use a condom?"

"I'm sterile."

"Where are my shoes?"

"You really don't remember last night, do you?"

"Did we have sex?"

Don't you hate those mornings you wake up and can't remember what you drank, who you fucked or what you did with your Coach purse?

And to not remember your first time? We'd almost feel bad for her if we all didn't know how hung Jess was.

It's probably better she didn't remember that. If that's what happened. We're not giving anything away

* * *

**Ending Author's Note**: Did I mention I was a bitch? That ending is probably the bitchiest thing, aside from killing Rory or Jess or revealing Jess didn't actually have a dick after such a long hiatus (I swear, it was so long, it was like I went on my own writer's strike) I could've done. But I couldn't resist ending that way because it sets up for flashbacks and confusion and pregnancy test and two versions of a story. Oh the goodies...if I ever update.

**Reviewers**: So, if you've ever pulled a Rory, do tell! I love hearing about regrettable bedfellows after drinking too much! I'm serious, too. This is all anonymous and good, dirty fun. If you tell me yours, I'll tell you mine. Also, thank you, for those that actually read, for being the most patient bitches ever. I know you were probably like "Bitch writes a story about someone losing their virginity and doesn't come through?!?!?! OMG WTF!" But we established long ago I was a bitch, so are you surprised?

So is Rory bluffin' with her muffin? Sorry, I had to do it.


	7. I Was Afraid I'd Eat Your Brains

Chapter 7: I Was Afraid I'd Eat Your Brains, Cause I'm Evil

**Author's Note**: So I disappeared again. This time I dropped some acid and played the tambourine for some random hippie band that played most of its gigs for squirrels and lost stoners. My hair got longer. I connected with nature on an almost sexual level. I was _this close_ to reaching nirvana. Then I woke up and realized it was just from some super awesome weed and I was still in my dorm room with Grace Kelly judging me from three different walls. But wouldn't that be sick if every time I fell off the face of the internet I had some crazy adventure? But at least my absence was short compared to two years, so really, we're making progress here. Since we last touched, I've fallen in deep love with Zach Galifianakis, become a pretend playwrite and gotten ridiculously close to turning 21. But you're not here to gather information for the biography I know you're secretly writing on me; you're here for THE STORY. Or what you remember of it.

Rory. Jess. Sexual tension. There; you're all caught up.

**Disclaimer**: Hipsters like _The National_. I like _The National_. Does that make me a hipster? Maybe. Whatever. Their music makes me want to be mopey in a way I never thought was possible. I love it. And the title comes from a song off their new album. If I ran the world (one day, I will), _The National_ would be appointed as the official band of angst.

The full title wouldn't fit in the chapter bar thing because it limits me. Seriously internets, stop limiting my creativity!

But enough of my babble. Let's solve that cliffhanger (are you still hanging? JUMP!)

* * *

Rory tried confession.

It didn't work out so well.

"I need God to forgive me and reinstate my virginity."

Aren't there ceremonies and surgeries for that?

"Excuse me?" Oh come on father, that's a fairly simple request, right?

"I swear, father, I went insane for a twenty-four period. I didn't choose to lose my virginity. Another me did. A slutty me parading around in an Oscar original," she paused. "I really hate slutty me."

"I don't think losing your virginity condemns you to being a slut, my dear." That's true. Perfectly good women lose their virginity all the time.

"Just say it. I'm a loose woman with no morals that Harvard is never going to accept. I'm going to be forced to go to some liberal arts school and experiment with lesbianism. I don't even like sushi."

"Um…"

"And the worst thing is, I don't even like the boy. Can you put some spell on him to turn him into a eunuch? He's going around with his filthy dick destroying the city's purity! That has to be a bother to the church, right?"

"I don't caste spells. I'm a priest, not a wizard."

"Can't you make a call on your God phone or something?"

"My God phone?"

"See, not only did this boy take my purity, but he's made me an idiot! I bet he gave me syphilis. Do you think he gave me syphilis?"

"Maybe you should go to a clinic and have yourself checked out if you think he's that unclean."

"And risk having it all over the internet that I have an STD? No thank you! Father, you've obviously never been a 17 year-old girl."

"My best advice then, for you, my dear, is to avoid this boy."

"Oh I will. Believe me. I loathe his smarmy self."

"I believe you."

"He's not even pretty."

Now Rory, have you lost your religion that quickly? Thou shall not lie.

"Well then, let's just chalk this up to a lapse of judgment. You have my permission to forget about it."

"Are you telling me to fake my virginity for whatever man I eventually decide is worthy of the company of my vagina? I'm telling the Pope on you!"

* * *

Then she decided to try the dry cleaners.

"I need you to tell me if this dress has any magical male discharge on it."

"You mean semen?"

"Keep your voice down! Did you not notice the sunglasses? I don't want people to know about my possibly semen coated dress."

"Why don't you get one of those black light things they use on CSI and check yourself?"

"Now you're being ridiculous! Isn't there some sort of test you can run that won't harm the dress?"

"Honey, if you let some guy blow his load on this dress, it'll never be the same."

"Did you have to say it like that? It sounds so vile."

"Why would a girl like you be having sex with a boy that would cum all over your Oscar De La Renta dress anyway? You're like Grace Kelly."

"Um excuse me, I'm definitely an Audrey Hepburn."

"Whatever. The point is, honey, I'm not running some test on your dress. I'll clean it for you but if you want to know if some boy used this as a target, ask a doctor."

"Let's role-play here for a moment."

"It sounds like you did enough of that last night," the lady muttered.

"I'm Sherlock Holmes. You're Watson. And someone killed a person with their semen. And that person was in this dress. If we find out whose semen is all over this dress, we find the murderer."

"How much semen did this girl swallow? I've never heard of anyone choking on semen."

"It was a hypothetical."

"And you're definitely a Watson. You're way too uptight to be Sherlock Holmes."

"Why do I even try with you people? Give me my dress back!" Rory said, grabbing the dress away.

"You might as well set fire to it. It'll always feel like it's covered in semen no matter what you do."

Always feel like you're covered in Jess' magical little men? Ew. No matter whom the semen comes out of, it should never be worn as an accessory.

* * *

Finally, she thought a "cleanse" might do the trick. And no, not a Gwyneth Paltrow cleanse.

"Miss Rory, I don't think an exorcism will solve your problems."

"Greta, I must have been possessed. Rory Gilmore would never let Jess Mariano touch her, much less…"

"But Miss Rory, maybe you're in love."

"Love does not exist. Besides, if I wasn't possessed before, his dick certainly put something in me that needs to be caste out."

"I don't think a priest will perform an exorcism on you because you had sex with Mr. Jess."

"Well then, Greta, what do you think I should do?"

"Talk to Mr. Jess about your feelings."

"I don't have feelings. Oh god Greta, what if I'm pregnant? I can't give birth to the anti-Christ, at least not before bikini season!"

"Well, did Mr. Jess, um, wrap his, you know, special friend?"

Rory grabbed her head. "I can't remember. I can't remember anything. All I know is I want my virginity back."

"Maybe you didn't lose it. What did Mr. Jess say?"

* * *

Five hours earlier.

"Well, did we fuck?" Rory asked.

"I prefer to call it making love."

"I would never have sex with you. I hate you." Oh little virgin. You've obviously never experienced the awesomeness that is hate sex. Well, until now.

"Oh I know. I have the scars on my back to prove it. "

"Fuck you."

"I'm going to need some Gatorade if you want to go another round. You fucked all the electrolytes out of me."

Rory picked up the discarded dress on the floor. A size four? Definitely not her, even after one too many croissants from Magnolias. "Where's my dress?"

"Men's bathroom. Downstairs."

"That's impossible. For one, I would never go in a men's bathroom. And two, I would never take off an Oscar original."

"Oh you didn't. I took it off for you. While you worked on my pants. You were a bit tipsy so I had to help you out with the belt. It was so cute."

Rory was trying to wrap her little mind around this situation. "So we fucked in the downstairs bathroom?"

"Once. Then again in the elevator. Then again in here. And then you passed out."

"Oh my god. Oh my god. Oh my god."

"You should be proud. You're by far my favorite deflowering. Even better than E."

"Wait, you took E's virginity?"

"She never told you?"

"I think I'm going to be sick." And then she fled to the bathroom.

* * *

"Do you feel differently?" Greta asked.

"I think I can feel the syphilis eating away at my brain."

"No Miss Rory, I mean, down in your special area."

"You mean am I experiencing vaginal discharge? I googled all the symptoms for Chlamydia and I think I'm safe."

"It is the silent killer."

"What?"

"Miss Rory, calm down. You need to sit. Now, what else did Mr. Jess say?"

* * *

"Let's order room service. I need something to soak up all that champagne."

He did work hard. All race horses deserve a snack. Or round two.

"I'm not going to share a meal with you," Rory spat.

"What about a drink? What's your stance on Bloody Mary's?"

Rory stared into the mirror, horrified. "You gave me a hickey? What are you, a vacuum?"

"It's called foreplay. And I think we're equal."

"How do you figure? I'm going to have to wear a turtleneck for a week!"

"I won't be able to be on my back for a week, which is going to put a wrench in my plans with Louise. And Jessica. And Andrea."

"You have a right hand. I think you'll survive."

"What about orange juice and some Advil? You at least need something for your hangover."

Aw, if we were naïve we'd confuse Jess' behavior with that of someone who was in love.

Rory marched out of the bathroom. "Why won't you leave me alone? You got what you wanted. I'm humiliated. Please, go away. You being here only makes this situation worse."

Jess took a step toward her. "Toothpaste."

"What?"

He took another step forward. "Put some toothpaste on your hickey. Wait thirty minutes. It'll keep you from having to rush off to Saks to buy a turtleneck."

"Oh."

"You look good, Gilmore," he brushed her cheek with his lips. "You look real good."

"Thank you."

"See, we can be civil. It is possible." He was dangerously close. One step and he could have her against the wall. "Do you still want me to leave?" he breathed.

She knew she had to ignore his existence. This was _so_ wrong. "Yes."

"Okay. Bye, Rory." And with that, he was gone.

* * *

"Miss Rory, he loves you!" Greta squealed

"Greta, stop it. Jess likes virgins. I was a virgin. Now I'm not. He did his job. He really should be a professional devirginizer."

"Was he good?"

"Greta! Completely inappropriate! Besides, I can't remember."

"Not even a little bit?"

"Well, there is one thing…"

* * *

Rory was leaning her ninety-pound frame against the door. Like that'd keep him out.

She took a swig from the bottle of champagne. "There is no way you'll get in here, Jess! I win! I win!"

"Rory, you weigh like ninety-pounds. If I wanted to, I'd have you on your back right now."

"Challenge accepted!"

"What?"

"I bet you can't get me on my back by the end of the night."

"Rory, you're drunk."

"Tipsy. There's a difference. I can still walk."

"Rory, just open the door, please. Your grandmother is about to have me thrown out."

"That's hilarious."

"Not really."

"I thought you were a bad boy. Are you a bad boy, Jess?"

"There are normally whips and cuffs involved when I get asked this question."

"You are such a whore, you know that? All the girls laughed when I told them you were my escort. By my calculations, you've fucked every girl under the age of twenty here."

"I get around."

"That's so much pussy."

"See, when you put it that way, it sounds meaningless. I remember most of their names. And if I don't remember their names, I remember their cup size."

"I can't believe I agreed to you being my escort. You're supposed to marry your escort! I can't marry a male prostitute."

With one quick push, Jess had the door open and Rory on her back, giggling.

"Way to spill champagne everywhere, Gilmore."

"You pushed me down."

"You kept calling me a whore."

"I'm sorry. You're a slut. I forgot you didn't get paid."

"Now I know why Logan fucks other bitches," he muttered.

"Do you like me?" Rory asked, out of nowhere.

"What?"

"I mean, I know you said you didn't love me. But do you like being around me?"

"You're entertaining."

"Like a stripper is entertaining?"

"You stimulate me intellectually."

"Have you been stalking me just so you could devirginize me? Taking my virginity would probably be your greatest conquest."

"Um, well…"

"You can have it."

"What?"

"My virginity."

"Give me your hand, Gilmore."

"So you won't fuck me either? First Logan, now you."

"Logan wouldn't fuck you?"

"Nope. I threw myself at him, because I thought that was what he wanted. I acted like a total slut. And what does he do? Slams the door in my face."

"Is that why you kissed me in the elevator?"

"Partly."

"Huh."

"Are you upset? Come on Jess, you're you. I'm me."

"What's that supposed to mean?"

"I'm supposed to marry Logan. And you're supposed to…"

"What?"

"Try to break up our marriage."

"I am such an idiot!"

"What?'

"You're not like all the others! What I said in the limo, I was lying. You're different. At first, I just wanted to fuck you. But now…I don't know. It's just different."

"Oh."

"That's it? I basically tell you I'm in some sort of like with you and you say 'oh?'"

"You told me you didn't love me! Do you know how hard that was to hear? And then in the limo you told me you were just taking me to the ball so you could fuck me. You said it. And now this?" Rory paused, then ran toward the toilet. "I think I'm going to be sick."

* * *

"And that's it. After that, it's all black."

"I know this doctor that specializes in bringing back repressed memories."

"This isn't repressed so much as alcohol erased it."

"But maybe he can do something. At least help you remember whether or not you had sex. It's worth a try, right?"

"Is he discreet?"

"Of course."

"Okay, make the call."

As soon as Greta left, Rory's phone rang. It was Jess.

"What?"

"Whoa, what's with the hostility?"

"I'm pretty sure you did things to me that are illegal in at least twenty states."

"Don't be ridiculous. Only the bible belt."

"So our sexual escapades all over my debutante ball are a joke to you?"

"It's hard to take a night completely seriously that involved you coming out and cumming in an elevator."

"I'm hanging up."

"Gilmore..."

She cut him off. "And if there's a sex tape, I will murder you."

"I can't control what they do or don't record in elevators."

"Oh my god."

"If it makes you feel any better, your performance was very Oscar worthy. I would call you the Meryl Streep of elevator sex."

"Goodbye, Jess."

"Meet me for dinner."

"No."

"Drinks."

"I'm never going to be seen with you in a public place again."

"Then come to my house. I promise I won't try anything. I just need to talk to you."

"Write about your feelings in your diary. I don't care. I have things to do, like get vaccinated."

"Just this once and I'll leave you alone for the rest of your life."

"That's what you said about the kiss in the elevator."

"To be fair, you unzipped my pants first."

"Fine. What time?"

"6?'

"You have ten minutes."

"That's all I need."

* * *

Of course there was someone behind this phone call. And that someone was a blonde, cokehead whore that couldn't be trusted around virgins. Or old women that were covered in diamonds and about to kick it.

"See, that wasn't so hard, now, was it?" E said, in her take over the world voice.

"Shut up, E." Jess said, in a tone that made it seem like he hated himself.

"Now just convince Rory you're in love with her."

"Rory's smart. She's not going to run into my arms just because I admit to having feelings for her."

"Oh trust me, she will. This is classic 'Rory is in love with you but doesn't want to admit it' behavior. She did the same thing with Logan in third grade."

"That was third grade. Rory's a bit different. She doesn't eat glue or dream about being the Pink Power Ranger anymore."

"You fucked her, right?"

"Yeah."

"Well then the hardest part is done. To be honest, I didn't think you could get your filthy dick anywhere near her purity without Tiffany's and a pre-nup, so well done, Jess."

"Please, leave."

"Why are you so upset? You got Gilmore's virginity! It doesn't matter what else you do at Chilton. You could accidentally fuck Gellar and you'd still be King."

"God, do you ever shut up?"

"Mariano, get your shit together. You are going to tell her you're in love with her. Then I'm going to tell Chilton about what you two did at her debutante ball while everyone else was still waltzing. And then you're going to tell her it was all just game. And that's how Rory Gilmore commits social suicide."

"You're the devil, you know that, right?"

"Rory would do the same thing if she was willing to prostitute Logan."

"Fuck off."

"I can't believe you actually fell for that bitch. Thank god you're incapable of actually being in a relationship or I'd have to plant some cocaine on her."

"Rory hates me. You didn't see her this morning. She is going to come here and beat me to death with her Chanel boots."

"We'll see. Worst-case scenario, she kills you, then kills herself. Then I just spin it as some Romeo and Juliet shit."

"I'm glad you have a plan in the case that I die."

* * *

And then, she appeared, as any folk singer would write.

"Okay Mariano, what's so important that you couldn't just tell me on the phone?" She stood in his doorway. Was she a vampire? Cross the threshold, Gilmore!

Jess didn't say anything. He just grabbed her face and kissed her. He kissed the hell out of her.

Rory stood there, letting him kiss her for the longest five seconds of her life. Then she shoved him into the wall, wiping her mouth with the back of her hand.

"What the fuck, Jess?"

"You can't tell me you didn't feel anything."

"I'm sure it takes more than ten seconds for throat syphilis to set in."

"Come on Rory. Stop fighting it. You want me."

"How many times do I have to call you an STD infested sloth before it sinks in? I hate you, Jess."

"No you don't."

"Don't tell me how I feel." Rory noticed Jess was slowly making his way toward her. "Stop."

"Stop what?" he asked, not stopping his movements.

"Walking toward me like _that_."

"Or what?'

She rummaged through her purse. "I'll pepper spray you."

"That's breath spray."

"It'll still burn."

"I'm not scared."

"You should be. I'm a crazy person. I'll spray you. Take one more step and I promise you'll be blinded."

"Nah, I'll just smell minty fresh."

He took another step.

"Jess," she begged.

"I love it when you say my name like that."

"We can't be together."

"When did I say I was looking for anything long term?"

"I'm not going to be your fuck buddy."

He started playing with her hair. "Okay."

"I'm not."

"Noted." He ran his fingers down her arm, making her shiver.

"You're the biggest mistake I've ever made."

"Ouch," he said, without any feeling. He leaned forward, placing a kiss on her cheek.

"I don't like you."

He ignored her, turning his attention to her shirt. It had buttons. Jess loved buttons. He started playing with the first. "Oops," he said, as it came undone.

"I have a boyfriend," Rory said, like it mattered.

"I know," he said, using one hand to undo the next button and the other to slam the door, forcing Rory into it.

"Jess, " she said, breathlessly.

"Rory, you're not wearing a bra."

She blushed, "I forgot."

He smiled. "Right." He had her against the door. She could feel him. All of him.

He finished unbuttoning her shirt and just let it hang off her body. Her heart was ready to rip out of her chest.

"I would never not fuck you."

"We can't do this."

"Why not?" he asked, searching for the zipper on her skirt.

"Side," she said, without thinking. He smirked as he watched her skirt pool at her feet.

"Wrap your legs around my waist."

"No."

"Okay," he said, sliding a hand under her La Perla underwear.

"Jess."

He put a finger to her lips. "Trust me, you'll like it," he said, latching his lips onto hers. She let her lips part slightly, forcing him to smirk into the kiss.

She wanted this.

She began to move against his hand. The most pleasure Rory ever got from Logan was when she put his phone on vibrate and played 'find your phone in my crotch' for his 16th birthday.

Their foreplay would have totally gotten Steve Jobs going.

He pulled away from kissing her. "Done this before, Gilmore?" he asked, because he could never miss the chance to be an asshole.

"No," she struggled out. "Never. Well, maybe once."

"So what are your feelings about the leg wrap now?" he asked, pulling his hand out of her underwear.

Ah, Jess, you can't tease the sexually repressed like that! Especially the newly devirginized.

"It's a bad idea."

Jess wanted her to wrap her legs around his waist so he could turn her around and have her on her back, straddling her in three seconds. He'd perfected this move. He'd also perfected sneaking out of windows right before the angry husband/mother/boyfriend walked in.

He was a talented man.

"It helps with the logistics of it all, Freckles." He pushed her shirt off her shoulders, waiting for her to decide. "You're perfect," he added.

She blushed, trying to figure out how to cover herself since he had her hands pinned to her sides. "I feel a bit underdressed."

He let go of her hands. "It does appear I'm a bit overdressed."

"You want some help with that?" she asked, grabbing onto the hem of his shirt.

"I never turn down a girl that offers to take off my clothes."

Rory pulled the shirt over his head, throwing it into the corner.

"Better?" he asked.

"Not quite." She moved her hands to his belt. "This is like a fucking chastity belt."

"I never understood why mother's want their daughters to wear dresses. It's so much easier for me to push up a skirt than to take off a pair of pants."

"So if you ever have a daughter, she's going to always wear pants?"

"Talking about my future lesbian daughter kind of kills the hot factor of this all."

"Don't worry; I don't plan on producing this fashion cursed offspring of yours."

"Good," he muttered, pushing her back against the door. "Tell me you want me."

"Why does it matter?"

"Because it does."

She started playing with the zipper on his jeans. "I came here with the intention of this being the last time I ever saw you. Not including pointing you out in a police lineup."

"Uh huh." He moved his hands back to her underwear, pulling them away from her hip, teasingly.

She wanted him to touch her. So badly. "Please, Jess. You know I can't say what you want to hear."

"Why not?" He asked, letting go of her underwear and backing away.

"Because we're not supposed to be together."

"Who says?"

"Everyone, Jess!"

"Fuck everyone! What do you want, Rory? For once in your life, do what you want!"

"I don't know what I want."

"Huh," he said. He sounded hollow. He threw her clothes at her. "Get out."

This was by far the most humiliating thing that had ever happened to Rory. Forget Logan's unwillingness to fuck her and throwing her into a wall. New Haven's biggest man whore wouldn't fuck her.

"What?"

"I can't do this."

"This is what you do! You fuck girls and then forget about them."

"I can't do that with you."

Rory didn't want it to end this way.

"I'm sorry, Jess."

"No, you're not."

A sob erupted from her chest. "Please, don't hate me."

He couldn't look at her when she cried. It was all too much. "I can't handle this, Rory."

"I wish I could tell you…"

"What?" When Rory didn't saying anything, he just shook his head. "He's not your Paul."

He paused. "I'm going out. When I get back, please don't be here."

And this time, he was really fucking gone.

As soon as the door slammed, Rory broke down.

Her mascara was ruined.

* * *

**Ending Author's Note**: So I've tweaked my style a bit. It's all a much quicker read since I've eliminated a lot of that side commentary. I know some people enjoyed the snarky asides, but the dialogue popped so much for me in this chapter that I just couldn't see the need to detract from it. It is the heart of this piece, honestly. I couldn't add anything better than the honesty that is bleeding out of these characters, especially in the last scene. So don't hate me for the change. Or do. But at least send the bomb wrapped in chocolate.

So whether or not they had sex at her debutante ball still isn't certain. Did you think it was certain? Did you trust Jess? Oh you silly readers. This isn't me saying he's lying. They might have done the deed. I won't tell...until I decide it's necessary. But if they did do it, do you hate me for not writing that sex scene? Probably. Again, all bombs must be disguised as something lovely. Like Zach Galifianakis.

**Reviewers**: This boat is sailing because of your love. Don't let the wind disappear beneath my sails or we'll crash and then I'll have to write some terrible _Titanic_ esque final scene that'll make us all want to commit suicide.

Also, I love you. Deeply.


	8. Where Have All The Good Times Gone?

**Chapter 8**: Where Have All The Good Times Gone?

**Author's Note**: I come to you from a land full of words and Oreos. And coffee. And the occasional Smiths song, to put me in the right frame of mind. I don't have much to say this time. I'm just a woman with a story and a dream. Or some bullshit.

**Disclaimer**: The title is deliciously spoilery of what is to come beyond these fun, little notes. And a Kinks song. So pour a glass of wine and say cheers to Ray Davies. And angst.

There are a few phrases I borrowed from _Gossip Girl_, cause they were too perfect to leave out of this mash up (that's what I'm calling it, btw. Tell your friends). They're so good, I use them in my daily lexicon as often as possible. Sometimes, I just yell them. "It was all a game!" during dinner is a big hit. Try it.

* * *

_Spotted: Jess Mariano back to his old ways._

Rory Gilmore watched from afar as Jess used the halls of Chilton as his own personal sexual playground.

She wasn't enjoying the show.

Paris came up behind her and frowned. "Jess' consistency is almost admirable."

"That's not the word I'd pick to describe his whoring ways."

"Do I sense jealousy in your voice, Gilmore? I thought you were over him."

"I was never into him."

"Right."

"I wasn't. He's a despicable human being."

"With really good hair."

"Whose side are you on, Gellar?"

"I'm on team honesty."

"Since when?"

"Since you fell in love with Jess."

"I'm not in love with Jess Mariano," Rory practically screamed.

Paris took a step back. "Then it won't bother you that in the past two days, he's fucked half the female population of Hartford."

"Nope."

"And that right now he has the poor man's excuse for Paris Hilton pinned against your locker."

"Well that does bother me. Because I'll have to pay someone to disinfect it."

"I have to hand it to you, Gilmore. You've rehearsed the 'Jess means nothing to me' speech quite well," Paris paused, leaning in, making her voice almost a whisper. "But everyone knows."

"Knows what?"

"About the real kind of cumming you did at your debutante ball."

"Excuse me?"

"Everyone knows you got drunk off champagne and fucked Jess. Multiple times according to some sources but I only believe about fifty percent of rumors so I'd say he got your v-card and departed."

"Who told you this?"

"Oh don't worry. I've been friends with you long enough to know to never believe a rumor without proof. Which is why phone's are so convenient," Paris paused, pulling out her phone, showing a picture of what appeared to be Rory, pinned against an elevator wall, with Jess' tongue occupying her mouth. "I never would've thought that the camera phone would be the death of Rory Gilmore. Damn technology, right?"

"I can't believe you're enjoying this."

"Being your minion for three years was…educational. But you're a complete bitch. You and Jess deserve each other."

"I'll destroy you."

"With what power? You've been dethroned. You're the Hartford Marie Antoinette."

"When I find out who did this, water boarding will seem preferable to what I do to them. And then I'll come after you."

Paris laughed, "I almost pity you, Gilmore. Wake up. This isn't some bad Audrey Hepburn movie. Your reign is over. But as your friend, let me give you some parting advice: get tested. I'd hate to see you go insane from syphilis."

Pairs turned to leave but then stopped. "Oh and headbands are so out. Take a break from fucking Mariano and read Harper's Bazaar."

* * *

Rory Gilmore was having what most clinical psychologists would call a panic attack.

Greta hadn't seen Rory like this since, well, E ruined her life and had sex with Logan. So this behavior could only be brought on by something like Hiroshima. Or the death of Alexander McQueen.

"Miss Rory, you have to stop pacing."

Rory attacked. "Greta! There is no time for activities like sitting. There are lives to ruin and you're just sitting there watching me."

"I'm afraid you're going to pass out. This is the most exercise you've gotten since…"

Going three rounds with Jess Mariano?

Greta continued, "…well, ever. You quit yoga after three minutes."

"I couldn't handle all that granola and downward dog. And hippies reek of compassion and hope, my two least favorite scents. How could I be expected to partake in some hippie orgy disguised as a yoga class? I'm pretty sure I saw Kate Hudson there! No thank you!" Rory adjusted her headband. "But enough of that! Someone has slandered the Gilmore name."

"What'd they say?"

"That I surrendered my purity to Jess Mariano!"

"Well, you did, Miss Rory."

"The evidence is inconclusive. And I know myself. Even at my very lowest and fueled by champagne I wouldn't let Jess get past second base."

"What about the other day at his house?"

Rory furrowed her eyebrows. "Have you been reading my diary?"

"It fell open when I was hanging your dresses."

"Okay, third base. Whatever. It's all the same. The point is Jess Mariano did not take the greatest gift I have to offer any man. Besides my company, of course."

"Do you think Mr. Jess told people?'

"I've considered that. I did humiliate him the other night by refusing to beg him to, um, do things that I would never do with him. But it's too evil, even for him."

"But he's your most formidable opponent at Chilton."

"Except for…"

Greta cut her off, "Miss E."

"Exactly."

"But how would she know?"

"Let's not lie to ourselves. I have about as many enemies as Stalin. I'm sure whatever pudgy bitch, marching around in an Oscar knock-off, that snapped the picture was more than willing to help out the devil."

"My family in Russia could make her disappear."

"As much as a service I would be doing the world to make that disease ridden whore disappear, there isn't enough death in suffering."

"Oh they'd make her suffer."

"I'm going to ignore that sparkle you get in your eye when talking about murder."

"Then what, Miss Rory?"

Rory didn't answer, distracted by her phone. And more specifically, who was calling her.

"Who is it Miss Rory?"

Rory's finger danced between answer and ignore, finally choosing ignore.

"Oh just a waste of sperm with less than honorable intentions. I'm surprised he took time out of his whoring to make a phone call."

"I think you're being a bit hard on Mr. Jess."

"Your job is to agree with me, Greta. It's why my mother pays you."

"Yes Miss Rory but…"

"You know what happens when people question Putin? They disappear."

"I can't help that deep down, I'm a romantic."

"Then go watch some bland film starring Drew Barrymore and Hugh Grant. Romance is for thirteen-year-olds that think a vampire stalking them is romantic."

"I prefer _The Vampire Diaries_."

"Do I seem like I'm in the mood to chat about sub-par network television?"

"Oh Miss Rory, but I think you'd like this show."

"We can watch it over the summer when my days consist of laying by the pool in the Hamptons and having a fling with a too tan for Manhattan lifeguard. Right now, we need to plot."

"Just return Mr. Jess' call and I promise to put all my energy toward getting rid of that bottle blonde bitch."

"Since you used lots of descriptive adjectives instead of her name, I'll indulge you this once. But I'm just going to tell him he is a sexual terrorist and hang up."

"You don't know how happy that makes me."

"Sarcasm is not attractive."

* * *

Jess picked up on the first ring. Way to not seem eager, boy. While you're at it, start humping her leg the next time you see her.

Rory started immediately. "Don't talk. You might want to talk about the mental breakdown I had in your room the other day. I don't. While it was mildly humiliating and resulted in the loss of my pride and Chanel earrings, which I want back, by the way, I've moved on."

"With who? From what I've heard, no one wants you."

"Is that your lame attempt at trying to hurt me?"

"Even I know you can't hurt a heartless bitch."

"How's it feel to know you're personally keeping the whores of Hartford in business?"

"Someone has to help them pay for college. I'm glad to be doing a public service. How's it feel to know you'll die bitter and alone?

"Comforting, actually. I'd rather be alone than the poor girl that accidentally marries you."

"Rory Mariano doesn't roll off the tongue that well."

"Fuck you."

"As much fun as this passive aggressive bantering is, and really, it's a thrill, I called for a reason."

"I'm breathless to hear what you have to say."

"I'd rather not have this conversation over the phone."

"What are you, pregnant?"

"Hilarious as usual, Gilmore."

"I'm a different person since I last saw you."

"It was only two days ago."

"I've done a cleanse and consulted my life coach. What happened with you was a phase. Nothing more."

"Bullshit."

"All I feel for you is pity because it's obvious you're fucking all these girls in an attempt to get over me. And failing."

"No, sweetie, I'm fucking them because I'm Jess Mariano."

"If it helps you sleep at night, go ahead, lie to yourself."

"The minute you see me, you won't be able to control yourself."

"I've been praying for you. I'm worried you'll end up drunk and roaming the streets, like Edgar Allen Poe."

"I thought you didn't care about me?"

"I don't. But to get over you, I had to forgive you."

"Forgive me for what?'

"You know what."

"My memory is a bit fuzzy. Give me a hint."

She sighed. "Why did you call, besides to give me a rash?"

"Meet me for drinks. In a very public place. I promise to keep my hands to myself."

"Why?"

"We have some things to discuss."

"Like how you told the whole school you took my virginity?"

He swallowed the truth and opted for a lie. "You know I wouldn't do that."

"Actually, I don't. You lied to me about fucking me and I believed you. Who knows what you told people that weren't even present."

"Whatever, Rory. Use whatever defense mechanism you need to protect your doomed relationship with Logan. But I didn't tell anyone."

"I'll meet you."

He was caught off guard. "What?"

"If you're telling the truth, I'll know."

"How?"

"It's a Gilmore thing."

"7?"

"I can't wait."

"Me either," he said but she had already hung up.

* * *

"Miss Rory, I thought you said Mr. Jess didn't tell anyone."

Rory stared into the mirror, applying red lipstick. "He didn't."

"Then why are you meeting him?'

"Because I have to finally end whatever there exists between us. I need him to set me free."

"He won't do that."

"I can be very persuasive."

"But even if he sets you free, if you still feel something for him, it's not going to be any different."

"I need him to tell me it was all just a game."

"But Miss Rory…"

"I'm a Gilmore. He's a Mariano. We aren't supposed to be together."

Greta sighed. "Which dress would you like to wear?"

"The black Chanel. It's his favorite."

* * *

Rory Gilmore knew how to enter a room.

Jess was determined not to notice her. He starred into his martini, refusing to make eye contact. He felt her heat as she closed in on him, felt her closeness, but still refused to look up.

"Gin martini. Dry,"she ordered.

"I didn't know you were a martini girl."

"I didn't know you were opposed to eye contact."

"It's a new thing I'm trying."

"How Japanese of you. Pick it up from one of your whores?"

"It fascinates me that you ordered Logan's favorite drink when meeting with me."

"It's symbolic."

"Of what?'

"How little you mean to me."

He finally looked up. "The other night, you couldn't tell me you wanted me. You didn't even stutter over the thought. You were more than willing to fuck me but you couldn't even admit to wanting me. It was like as long as you didn't verbalize it, it didn't count. You knew how I felt about you. You knew and you just stood there, crying, begging me to understand why we could never be together, like it was a law or some bullshit like that."

Rory didn't expect this. "Um, well…

Jess cut her off. "I fell in some sort of love with you. I hadn't fucked anyone since your mother's party. A fucking nose graze and I was a different guy. What is wrong with me? I knew you didn't want me but for some reason, I couldn't get you out of my head. All I thought about was how much I wanted to be inside you, how I wanted to be the guy that saw the look on your face when you lost control. And then you asked me to be your escort and fuck me, I thought that meant something. But it was all just a game."

"That's all we were. Just a game," Rory whispered.

"That's all you can say?"

"What do you want me to say? That I'm thrilled you took my virginity and I don't even remember? That I wanted it to be you? That I'm happy it was you and not Logan? That when I think about you I can't even breathe? Is that what you want me to say? Because I can't, Jess! I can't."

"Why?"

"Because it's too much. I can't be…I can't…it's not safe."

Jess touched her thigh. "I know you're on fire right now. I can feel it. Don't deny it. Stop denying it. For once, Rory, be honest with yourself. Please."

"Yes, Jess! I want you. I want you so bad it makes me hate myself. You make me hate myself," she paused, removing his hand, "which is why I need you to set me free. Tell me I meant nothing to you. That you did all of this just to fuck me. Please."

"Is that really what you want to hear?"

She didn't hesitate. "Yes."

"I wanted you because my best friend couldn't have you. I wanted to wave your v-card in his face," He stopped, trying to gain composure, "It was all just a game."

Rory couldn't breathe. "Thank you."

Jess stood up. "You're welcome." He went to leave, then stopped. "Your virginity is still intact."

And then he was gone.

Rory's head fell into her lap, sobs taking over her tiny frame.

* * *

One week later.

No one, not even the Russian call girls he so adored, had seen Jess Mariano since his encounter with a certain virgin. Yes, we said virgin. It appeared Jess couldn't get where no man had gone before, which was really a shame because we were so looking forward to referring to him as Neil Dickstrong from now on. Oh well. We should've known Gilmore wouldn't hand over her virginity to someone that in no way resembled Carey Grant.

Jess Mariano gone. This had to be cause for celebration for the virgin. Right?

"He won't take my calls."

"Who?" Greta really was Rory's only friend.

"Jess."

"I thought you finished things."

"I did. But it's Jess. He's probably stumbling around Brooklyn in a haze of whiskey, smelling like a baby prostitute. As the only friend he has, I'm concerned."

"I thought you were no longer friends."

"Did I say friend? I meant…well, I don't want him to get hit by a fast moving vehicle! Is that so wrong of me?"

"Oh Miss Rory. Just admit it."

"What?'

"That you're in love with Mr. Jess."

"No, I'm in love with trunk sales and iced coffee and Russian literature. Not Jess Mariano. Never."

Greta had watched Miss Rory wallow for years, ever since she first saw _The Way They Were_ and decided to emulate Barbara Streisand. She knew how to appeal to her somewhat dramatic tendencies. "When Mr. Jess gets in a bad way, isn't there a bar he frequents in Brooklyn?"

"I'm not going to rescue him! That makes it seem like I'm worried. Which I'm not."

"Then I'll go inside, look around and see if he's there. It'll be simple. You can wait in the car."

"Make sure he's breathing."

"Of course."

"Because that bar is wretched. Audrey Hepburn wouldn't be caught dead there. You really shouldn't even go inside. But I'll make an exception this once…wait, what was I saying? Oh yes. The bar is so despicable that he could be shooting up like Charlie Parker in the corner and they'd be oblivious."

"What do you want me to do if he's shooting up in a corner?"

"Jess would never do hard drugs. He's Kerouac light," she paused. "Oh and let me know if he is in the company of anyone that wouldn't be allowed near my grandmother." She stopped, and then realized what she had to do. "You know what? I'll just go inside."

Greta smirked, "If you're sure."

"If he's in a bad way, I'm the only one that can get through to him."

Really, she just couldn't be away from Jess any longer. She'd made a mistake at the bar. A huge, awful, irreparable mistake.

* * *

The bar was named Rick's. How appropriate.

Rory saw him as soon as she entered. He stood out, being the only guy who had ever heard of Hugo Boss and still tried to wear a bow tie after ten gin and tonics.

"Rory Gilmore in Brooklyn. I must be dead."

"I'm sure you're only one vagina and a gin and tonic away."

"What brings you to this fine establishment?"

"You."

"But it was all just a game, Freckles. That I apparently lost," he said, mocking her turn of phrase.

"You can't do this."

"Why do you care what happens to me? You're not my girlfriend, my friend or even a girl I fucked. You mean nothing to me."

Rory stiffened. "I don't believe you."

"Don't get me wrong; it would have been nice to have taken what was oh so precious to you. But I failed. And I've decided to move on. I have new conquests to occupy my bed with."

"How noble of you. And while I fully support your mission to fuck every bitch in Hartford, it's kind of hard to do that from some bar in Brooklyn."

"So you're here to play some twisted version of a wingman?"

"Sure."

"No, thanks."

"Come on, Jess. Even Elliot Smith would peg this as pathetic behavior."

He lifted his gin and tonic. "I'm just a man enjoying a drink. Hemingway partook in this activity quite often. He's your hero, right? The one thing that always seems to get you going? You should approve of this behavior."

"Hemingway shot himself."

"He didn't fade away. It's commendable."

"Fine. Sit here and wallow in self-pity. But if you ever decide to sober up, I'll be in Hartford."

"You seem to confuse me with someone that cares about your whereabouts. I'll admit, I had a thing for you. You had this unattainable quality, an innocence that I wanted to take. And seeing you in nothing but your panties is an image I continue to play over and over in my head," he paused. "But that's all you are to me; an image of perfection. Once I got to know you, I wanted nothing to do with you. I don't want you or your pity."

And then, for the kicker. "By the way, Gilmore, this was all just a game orchestrated by the lovely E."

She was confused. He must be drunk. "What?'

"E asked me to fuck you. Not that it was that excruciating of a task and I quite enjoyed parts of it, as you know," he looked her up and down in a way that made her feel naked, "but the only reason I was in detention that day and followed you into the bathroom and held the elevator was because I was doing what E wanted. The plan took a bit longer than expected since you were more immune to my charms than every other girl at Chilton, which is impressive, but like all the others, by the end, you were practically begging me to fuck you. The only reason I didn't was because I hate E. She really is a cunt, worse than you, actually. But if I'd wanted it, I could have been the proud owner of Rory Gilmore's virginity."

"You're lying."

"It was all just a game, Rory. Enjoyable for a while but by the end, I was tired of your shit, just like everyone else. It's almost sad to think that you're only friend is someone your mother pays to follow you around. How does it feel to be completely alone?"

She fought back the tears. "I can't believe I was considering the idea of being in love with you."

"I'm a good actor. I don't blame you."

"Shut up. Just shut up." She grabbed her head. "How could you do this to me?"

"I always told you we were the same. It's your fault for not believing me."

Rory grabbed his gin and tonic, tossing it in his face. "Never talk to me again. Don't look at me. Don't think about me. If you see me on the street, turn the other way. And if you ever speak about anything that happened between us, I'll destroy you."

Jess, finally, had nothing to say.

"Goodbye, Jess. You'd be wise to not come back to Hartford."

Rory turned, running out of the bar, her heels slamming into the mahogany floor.

Jess watched her run. He looked dead inside.

Picking up his phone, he called E. "It's done."

"How'd she take the news?"

"How do you think?'

"I'm guessing I won't be getting an invitation to the wedding."

"Even if I wouldn't have made a deal with the devil, we never could've worked."

"I'm glad to see you've spent enough time with Gilmore to adopt her Audrey Hepburn fantasies. How's it feel to not be her Paul?"

"Wonderful," he said, without any feeling left in his voice.

"Well, I guess this is it."

"Enjoy ruining any man with potential."

"Enjoy sorting out your mommy issues with a slew of Russian call girls." E stopped. "I still can't believe you're so in love with her you were willing to sacrifice yourself to get rid of me."

"Like I said, we never had a chance."

"If only she knew, maybe she'd forgive you."

"She knows enough."

"Yeah, and I'm not the romantic type, so it's not like I'm going to tell her…"

He cut her off. "Goodbye, E." He hit the end button. It was symbolic of so much more than he wanted it to be.

Jess hated symbolism.

"Another gin and tonic," he ordered.

This was all he had to live for.

* * *

Paris sauntered up to Rory with a coffee. She pushed it toward her. "A peace offering."

Rory stared at the coffee for a bit, wanting to make Paris squirm, finally deciding to accept the gesture. "Why the sudden change of heart? I thought you found a new queen."

"She left town."

"E's gone?'

"I guess she really wasn't ready for the much anticipated showdown with you."

"Do you know where she went?'

"Probably back to that convent. Or a mental hospital. Supposedly she had a mental breakdown in Charleston's office, confessed she made up the whole "Rory Gilmore has found company on Jess Mariano's dick" story and was asked to find help."

"How pathetic."

"I should've known you would never sink so low that you'd let Jess Mariano take your virginity. You're a Gilmore."

"He took E's virginity. And half the girl's at Chilton. I'd have to be completely consumed by my pseudo daddy issues to ever go there."

"I'm prepared to beg for your forgiveness."

"Good."

"You seem oddly calm about the whole situation."

"I've changed."

"Don't tell me you've adopted some hippie type philosophy full of love and compassion."

"God, no. Kill me with a sharp object if I ever start smoking hookah with unsavory characters and hugging dogwoods."

"I'm pretty sure that is in our constitution."

"That reminds me; we need to find our next project."

"I'm thinking about Karen O'Hara."

"Terrible name."

"We could probably get her to change it."

"Look into the logistics of that."

"Will do. Anyway, she's always photographed in the front row at New York Fashion Week. She's never been seen in last year's Kate Spade's. And her father is good friends with Donald Trump."

"What about her breeding?"

"I can't find anything on her mother."

"Probably means she was a whore."

"Or dead."

"So we have a Cinderella on our hands?"

"But with a trust fund."

"It could work."

"If you don't mind me asking, why do you want to find a new minion so quickly?"

"I'm bored with the complacent social order of this school. People have gotten too comfortable with their supposed importance."

"You're going to make such a good dictator one day."

"Thank you."

Paris paused, unsure of her next question, but posed it anyway. "I know this is dangerous territory to breach and you don't have to answer but I have to know, was there ever anything between you and Jess? I mean, I know you didn't lose your virginity to him but there was a certain tension between you two for some time. He's charming, rich and from what I hear, well-endowed, so no one would blame you for being briefly enamored with him."

"Why do you care? Are you writing fan fiction about Chilton?"

"No, I just…"

"Don't mistake being my minion with being my friend. We're not confidants. I don't even really like you. Next time you side against me, I'll make sure to make every minute of your life unbearable. Do you get where I'm going with this?"

Paris rolled her eyes. "We're not going to sit around and gossip and braid each other's hair. Yeah, I get it."

"I'm glad. Never bring up Jess again."

"Okay." Without answering Paris' question, Rory just did.

* * *

But no matter how hard Rory tried, there was no way she could avoid Jess forever. They had a way of getting thrown together.

Rory was pacing in front of Charleston's desk. "This is bullshit. Complete and utter bullshit."

"You skipped 6 of your 7 assigned detentions. And you were drunk at the one you actually attended. This is your own fault, Miss Gilmore."

"I've been accepted to Harvard. I'm done with this place."

"Lower your voice, Miss Gilmore. And adjust your attitude. You still have a month left here."

"You can't make me complete this bullshit punishment. Miss Rigby made the whole thing up! She confessed."

"While that is the case, your behavior, when confronted, is what landed you in detention. You acted like a petulant child."

"Do you know what I've been through since you allowed Miss Rigby back into what is supposed to be an exemplary institution that prepares its students for Harvard, not a future in porn? And not even good porn at that? She tried to ruin my life. She paid someone to try and take my virginity! Do you know how humiliating that is?"

"Oh dear lord, did he succeed?"

"No! But think of the implications if he had. And I'm still being punished. And I broke up with my boyfriend and took someone else as my escort to my debutante ball that doesn't love me and never will and never did and was paid to take my virginity. Do you understand?"

"Someone was paid to take your virginity, yes."

"So you can't make me to go detention. Or I'll kill myself."

"What?"

"Not really. Don't put me on Xanax. I'm fine. But metaphorically, I'll kill myself."

"I don't follow."

"Why is this school out to get me? I'm a good person! I'm the valedictorian. I volunteer at soup kitchens. I'd save kittens from trees if I wasn't afraid of heights."

Charleston sighed. "Just go to detention today and I'll write off the other five as served, okay Miss Gilmore?"

"You're such a dictator."

"It was lovely seeing you, Miss Gilmore. Say hello to your grandparents for me."

"Nazi sympathizer."

"I look forward to your speech at graduation."

"Say hello to Eva for me," she muttered, slamming his office door.

* * *

"Oh, you've got to be kidding me." Rory slammed the door behind her.

There he was. The dick she banished from Hartford. In detention. With her. Again.

_We're guessing this time there isn't going to be any rum. Or fun. Oh well. _

"What'd you do this time, Gilmore?'

"Don't speak to me."

"You asked me a question."

"It was a statement, jackass."

"Still bitter, I see."

"Let's see. You plotted with E to take my virginity, pretended to be in some sort of love with me, subsequently making me dumb enough to develop pseudo feelings for you. And then humiliated me in a bar on Brooklyn. Did I leave anything out?'

"Am I allowed to speak?"

"If you must."

"Well, the almost sex in my bedroom was an important moment in our fake relationship, I'd say."

"And your murder right now will be added to that list, I'm sure."

He thrusted toward her. "Your hate of me has always turned me on."

"Who's paying you to fuck me now?"

"Your mother. She thinks a good fuck is just what you need."

"Does she know she employed the worst prostitute in town?"

"I'm guessing you're not planning on forgiving me anytime soon."

"I thought about it. But then I remembered that time you were paid to fuck me and decided against it."

"I wasn't paid."

"You whore yourself out for free?" she asked, rhetorically.

"It's not like you're innocent in all this, Gilmore."

"Actually, I am. Have you forgotten that you failed at the one, important task in your mission?"

He rolled his eyes. "You know what I mean. I wasn't going after a poor, defenseless virgin with headgear and a skin condition. It's you. You make grown men cry."

"My ability to bring people to tears doesn't make my virginity a betting matter."

"I'll admit what I did was…"

She cut him off, "You treated my virginity like it was a race horse!"

"You used me just as much as I used you, Freckles."

"Excuse me?"

"That night in my room…"

"I had a mental breakdown."

"Well during that mental breakdown you practically begged me to fuck you, as long as you didn't have to admit to having feelings for me."

"It's hard to develop feelings for a spineless jellyfish."

"You know how I feel about you."

"Whores don't have feelings."

"I don't know why I try," he muttered.

"You mocked me in the meatpacking district. People don't recover from that."

"You're the same heartless bitch you've always been, so I say you recovered just fine."

"You can't do this! Stop it! You can't tell me I meant nothing, that it was all just a game, that you were fucking me for sport or some shit like that and then try to spin this into some mutual fuck up. I get to hate you. It's my right. You don't get to be bitter."

He sort of smiled. "I love you."

"What?"

"You heard me."

"I'm going to pretend I didn't."

"I get that what I did to you is classified as unforgivable by most human beings. But we're different. You're different. Stop pretending that we operate under the same rules as everyone else."

"I don't love you."

"You don't mean that."

"Yes, I do. I thought I did but it turned out to be a cold."

"So you loved me…"

"For four to six days."

"I don't want anyone else." He was practically begging at this point.

"Well, that's too bad. Because I don't want you," she said, without any feeling.

"I'm sorry."

Rory looked down, "I wish I could forgive you…" she trailed off.

In three seconds, he had crossed the room, closing the gap between them. He grabbed her hands, a hopeful look in his eyes. "You can."

When she didn't say anything, he continued. "Who cares what everyone else thinks? I want you, Rory Gilmore. You. That's all that matters."

"Goodbye, Jess," she whispered.

He was confused. "What?'

"You make me miserable. I can't be with someone that makes me miserable." She jerked away and turned, leaving him behind.

* * *

**Ending Author's Note**: And that is the end.

Just kidding. I'm not that evil. Although I'm not promising a happy ending. Just that the next chapter is the end, the end my friends, as Jim Morrison would say. I'm really happy that it just sort of naturally progressed to this point. It's so strange how a story really writes itself, if you let it. I understand the need to please fans or get a story to a certain conclusion or have two people end up together but with this story, I really haven't done that. Basically, I destroyed every relationship in this chapter and burned the whole fucking thing down cause that's what the story wanted me to do. I know I sound possessed right now, like I'm writing some Stephen King shit ("The story made me do it!" I'll scream from my padded room) but I really understand that Hemingway quote where he says all I do is sit down at the typewriter and bleed or something like that. I just provide the words and somehow, it became this. This mess. Whether or not you like it, well, I have no way of knowing (until you do that whole review thing) but I hope it at least feels real, like nothing was forced.

So the next chapter. The end. It'll probably take me a month but it's coming. Finally.

**Reviewers**: I feel pretty shitty about never responding to your lovely reviews because without you guys, I wouldn't do this. I need some sort of support and you provide that. This is a truly hippy experience, brimming with love and honesty and neediness. It's glorious. But this time, I promise to take the time and respond to your thoughts/concerns/ideas. Because I really do value them and look forward to them. So thank you and sorry for failing last time. Now, shall we go out with a bang? I say yes. Bang the shit outta that review button. And then I'll bang the shit outta the reply button.


	9. The Beginning After The End

**Chapter 9**: The Beginning After The End

**Author's Note**: It all came so soon-that's what I'm supposed to say, right? Too bad I waited two years to complete this masterpiece (yeah, I just called it a masterpiece, because why be humble, now, at the end). Still, I'm going to miss writing this trashy, over-the-top, flashy little piece of Russian literature inspired fan fiction. This is how I truly express misery. Just kidding. All my writing is pretty damn miserable. But here I get to be even more ridiculous. I'm riding a unicorn through a strawberry patch, fucking Ed Westwick, when I write this story. More or less. Mostly less but whatever.

**Disclaimer**: The title comes from a lovely little Stars instrumental piece. It was going to be _I Know It's Over_ but I was listening to this song and was just like, holy shit, this fits everything I want this story to embody so perfectly. I hope the connection hits you over the head cause we ain't about subtlety right now, bitches.

* * *

Logan should be having pity sex right now. His best career move, sexually speaking, was pretending Rory stomped all over his heart. All he had to do was appear, looking like he'd spent the day in bed, listening to Elliot Smith, contemplating suicide, and girls would flock to him, soothing his heartbreak with their vaginas.

But last night, while they were getting high, Finn started babbling about how obsessed Jess was with Rory and how obvious it was she was into him and how Jess fucked her right after her debutante ball. While they were still, technically speaking, since he was probably getting blown by Louise at that very moment, dating.

Sure, Logan treated Rory like shit and cheated on her whenever the option was presented but he loved Rory. And Jess was his best friend.

Your best friend does not fuck your girlfriend. It just doesn't happen.

And if it does, you have to kill said best friend. Or at least beat the shit out of him. Which Logan was about to do.

"Jess, a word?"

Logan gestured toward the brunette that was currently attached to Jess' neck. "I'm busy," he muttered, more interested in this girl's actual bra size (he was guessing 34C and was fairly certain he was right, since he was an expert and all) than whatever his fake best friend needed to discuss with him.

"She'll still be here when you get back."

Jess groaned, and detached the vampire from his neck. "I'll be right back. Don't rebutton anything."

Logan dragged him into a corner, away from any type of distraction, like a nice pair of 34 D's that would make him leave Miss 34 C unbuttoned and unsatisfied.

Jess shrugged his way out of Logan's grip, pissed off. "What?"

"I've been hearing things."

"I believe that's called insanity. Can I go now?'

"Did you try to fuck Rory?"

"Excuse me?"

"Because friends don't fuck each other's girlfriends."

"That clause is malleable depending on the girl."

"So it's true?'

"No, I didn't fuck Rory," he sighed.

"Thank god."

"I could have. But I didn't, since I'm such a gentleman."

"Rory would never touch you."

Jess didn't want to fight. He wanted to fuck Miss 34 C (or at least get a blow job) and the longer he stayed here, discussing whether or not Rory Gilmore would let his filthy dick anywhere near her, the more likely it was Miss 34 C would realize she was practically getting fucked in public and promptly rebutton.

But he couldn't just stand there and let Logan insult his dick giving abilities. "Didn't Rory break up with you?'

"We're taking some time apart."

"And remind me, who was her escort to her debutante ball?"

"She was using you to make me jealous. And you're so pathetic, you went along with it."

"Did you ever touch Rory the entire time you were dating? Because she was practically begging me to fuck her."

"Shut up."

"She makes the cutest face when she's about to cum. I should have taken a picture, but my hands were occupied, if you know what I mean," and then he winked, for effect.

Male aggression was such a wonderful thing. All that built up testosterone could only be released two ways and Jess and Logan certainly weren't going to fuck.

Jess felt Logan's fist connect with his face. It was just what he wanted.

Logan coiled away, shaking his hand in pain. He really was a pussy.

Jess was practically giddy, nursing his soon to be black eye.

"Why the fuck are you smiling?"

"I can't believe I'm fighting with you over Rory. You. You're barely literate. Why the fuck did Rory ever spend any significant amount of time with you?"

"Does she know she needs to be tested after being within fifty feet of you?"

"She doesn't want you, Huntzberger."

"She doesn't want you either."

"Maybe not now. But she will."

"What does that mean?"

"It would take too many syllables to explain to you."

"Excuse me?"

"You wouldn't understand."

* * *

Jess watched, amused, as Rory paced in front of the coffee shop, muttering to herself. He was fairly certain he knew what was going on. Rory had spent three blissful months tanning and developing an eating disorder and not thinking about Jess Mariano.

But on her second to last day in Hartford, there he was, in her favorite coffee shop, the only coffee shop she trusted, reading, at her table. Her table. It was a well-known fact around Hartford that Rory came to this coffee shop everyday at 9:54, ordered an iced coffee (maybe two if she had too much vodka the night before) and then sat at the corner table, in hopes to avoid all human interaction. And read.

The point was, it was 9:54 and Jess was occupying her fucking table.

"You can do this, Gilmore. Just walk in, get your coffee and kindly ask him to get the fuck out. He won't want to make a scene." Then, she slammed her palm into her forehead. "Of course he wants to make a scene. The whole purpose of him being here at 9:54 and sitting at your table is to make a scene."

She tried to steady her breathing. She didn't need to pass out and awake to Jess standing over her, pretending to be a knight in shining armor, when really, he was a leech infecting the world with his brand of dreadfulness and syphilis.

She could just go somewhere else. There was another coffee shop five minutes away that…made their coffee too weak and only played Lady Gaga.

Fuck if she was going there.

"This is my coffee shop." And with that, she threw her sunglasses back on, looking more like Holly Golightly than usual, and barged in the door.

Jess smirked. "Quite the performance out there."

She stood there for a moment, thinking. Then, to the surprise of everyone, she collapsed into the chair. "I'm so tired of this." She took off her sunglasses.

"The sexual tension is overwhelming."

She gave a sarcastic smile. "Do you know how hard it is to avoid you? I had to make maps and charts and have Greta go into any bookstore first and then send a signal saying it was okay to enter. I even considered attaching a chip to your body so I would know where you were at all times but I didn't feel like hiring a prostitute to get _that _close to you. My whole summer has been dedicated to avoiding you."

"My whole summer has been dedicated to…"

"Fucking in my general vicinity?"

"Pretty much."

"I would turn a corner and there you'd be, mauling and groping some whore. All tongue and hands and general indecency. It was disturbing."

"Thank you."

She smiled, genuinely. "I'm going to get an iced coffee."

"I know."

"I wouldn't mind if you stayed."

"Really?"

"Even bitches need human interaction."

"Been a lonely summer?"

"According to the gossip hounds, my eating disorder has taken up most of my time."

"You are looking a little thin."

"I went through a phase of not eating."

He raised an eyebrow, genuinely concerned.

She shrugged. "It's a girl thing."

* * *

Rory sipped her coffee. "I heard about your fight with Logan."

"I wouldn't call it a fight."

"I heard there were punches thrown."

"A punch. It was weak. Logan just needed to assert his pseudo dominance. And I let him."

"I heard the fight was about me."

He smirked. "Your hearing is impeccable."

"I don't need you going around, defending my honor. You're not my boyfriend," she spat out, full of venom.

"I know."

"I'm sorry," she said, out of nowhere, losing the venom.

He was caught off guard. "For what?"

"That black eye. It's my fault, for…"

"Stringing both of us along?"

She looked down, even though she wasn't really ashamed. "Yes."

"Well, I appreciate the apology. But it was worth it to see the look on his face when I told him about that time in my bedroom."

"Jess!" she squealed.

"I didn't lie! Everything I said was factual."

"I doubt it."

"I took your clothes off. I made you cum. Basic facts. I didn't say we fucked."

"Good."

"I said we almost did."

"Great."

"Pretending nothing happened would be dishonorable."

"You didn't seem to have a problem with being dishonorable a few months ago."

"I'm trying to be a better person."

"And to do that, you needed to swing your metaphorical dick in Logan's face?"

"Why are you getting all worked up? It's not like you're dating the guy."

She raised her voice. "Because you're acting like my boyfriend! If you keep this up, I'll never lose my virginity!"

"So you're mad because you want to fuck Logan?"

"No! I just don't want to have some hex on me making it impossible to move on! It's not fair that you've fucked every unassumingly pretty bitch in the city and I stayed at home, listening to _The Smiths _and watching terrible vampire soaps with Greta!"

"I want you to be happy." He seemed sincere.

She looked away. "I don't think I'll ever be happy."

"Me either." Jess leaned across the table and brushed her cheek with his lips. "We're not over, Gilmore," he whispered.

She coiled away. "I'm not going over this with you. Again."

She was about to leave, but he grabbed her wrist. "Just one night."

"What?'

"We need this."

"A one night stand? No, thank you."

"That's not what it 'd be with us. It'd be closure."

"I'm not longing for any type of closure with you."

"Bullshit." Jess stopped, then continued. "We can't be together right now. I get that. I fucked that up. It probably wouldn't have worked anyway. You'll go to Harvard, meet some asshole that'll seduce you with Tolstoy and forget about me."

"And you'll fuck anything with a pulse."

He laughed. "See, that's where you're wrong, cause if I had you, I wouldn't need anything else to satisfy me."

She blushed. "I'm not the type of girl that sleeps with a guy to give him closure. In case you forgot, I'm a virgin."

"Do you really want some pseudo intellectual, that'll end up being gay sophomore year, taking your virginity?"

"Why do you care?"

"You know why."

"Why can't you just give up?"

"Because you're all I want."

She blinked, trying to find words. Words to explain why this couldn't happen. "If we do this…it'll…it'll just ruin everything."

"The romanticization of unrequited love is overrated."

"I'm pretty sure you're the only person in the world that believes that."

He laughed. "Only a virgin would say something like that. Fucking is…well, awesome."

"Do you have to be so crass?"

"Do you have to be so proper?"

"We're not having sex!" she screamed, garnering the attention of a few too many fellow coffee enthusiasts.

He smiled. "I wish you could comprehend how hard it is for me not to kiss you right now."

She looked down. "You're a sexual deviant."

"You look good, Gilmore. Real good."

"Compliments won't get you in my pants."

"O-k-a-y," he said, drawing out each syllable in a way he knew annoyed her.

"Don't do that."

He sighed, ready to give up. "I'll see you around, Rory."

He was about to leave, when Rory stopped him. "Wait."

He sat back down. "What?"

"If we do this, no one can ever know."

"My lips are sealed."

"I'm not saying we are doing this. I'm just saying if you happened to stop by my going away party tonight and I happened to have a bit too much champagne and things happened, well, it just stays between us. Okay?'

"Don't worry, lover, I won't fuck and tell."

"Don't refer to me as your lover. We're not lovers."

Jess stood up. "Tonight, I'm gonna fuck the bitch right out of you."

And with that great parting line, he left.

* * *

She downed a glass of champagne.

And another.

And another.

She had decided she needed to get good and drunk, so if she went through with this, she could just use the excuse "I was drunk. He was pretty," even though the real excuse was "I was horny. He was pretty."

There he was, standing in the corner, discussing something intellectual with her grandfather. This was too much for her to handle. Jess couldn't exchange pleasantries with her grandfather. If her grandparents approved of him, that meant they'd have Hartford's blessing to fuck.

She wasn't okay with that.

Something had to be done.

Steadying herself, she took one last sip of champagne and made her way over to Jess.

"Grandpa."

"Rory. I feel so honored to be in Miss Harvard's presence. Don't you, Jess?"

He was too busy undressing Rory in his mind to come up with something witty. "Definitely."

Rory rubbed the back of her neck, trying to ignore the fact that Jess was violating her with his eyes. "What were you two discussing?"

"You," her grandfather answered.

"Me?'

"What else would we discuss?"

She blushed. "Oh, I'm not that interesting."

"Why are you being so humble, dear? It's not becoming."

"I'm sorry."

"Apologizing is even less becoming."

Rory would have been offended but her mind was full of champagne and Jess and whether or not her virginity would be intact by the end of the night.

And Jess.

And his hands.

She faked a smile, turning her attention to Jess, who looked like he was ready to take her, right there, in front of her grandfather.

Something took over (probably the champagne) and she reached out, grabbing his hand and dragging him toward her bedroom.

Richard smiled. He had never really cared for Logan.

* * *

He slammed her against the door.

His hands were everywhere.

She couldn't catch her breath, not that she really wanted to.

She was the one that invited him to her bedroom, to come look at some book.

That was her line, actually. "Come look at some book."

And he followed.

He pushed her against the door, again, and this time, she couldn't help the tiny whimper that escaped her mouth. Not wanting to break the kiss, he mumbled "sorry" into her mouth.

She responded by pushing against him, harder, so she could feel exactly how much he wanted her.

But right when his hands found his favorite spot, her ass, she remembered all the people that were outside her door.

Her grandparents. Her mother. Logan. All the people that knew what "some book" was code for.

Rory pushed him away. "This is twisted."

He couldn't help but smile. She never abandoned that Audrey Hepburn propriety shit, even when she was grinding against him. "Did you expect anything different from us?"

She stepped away from the door. And him. "This isn't what normal couples do."

"You've got to stop trying to define us in the realm of normal. And we're not a couple."

"We're a couple of people that like to take off their clothes in front of each other. I don't know how else to properly define that."

"Human."

"You're killing the moment."

"I believe you already did that when you called this twisted."

"I thought that would turn you on."

"There are other things you could do that would be infinitely more affective at turning me on."

"Like?"

He backed her toward the bed. "You sorely underestimate the power of you."

"What?"

Her knees hit the back of the bed and buckled.

He was leaning against her, so close that she could feel him, all of him, through her sundress.

He could hear her heart beating. It sounded like it was about to rip out of her chest. "Are you scared?"

She was caught off guard. She didn't want to be vulnerable. "No."

"It's okay. It's going to be okay." He pushed against her once more, just enough so she fell back onto the bed. He followed, hovering over her, letting her feel his weight on top of her.

He pushed the material of her sundress up her thighs, roaming his hands over the exposed skin.

She started to fool with his tie, then let go. " I'm sorry. I'm not good at this."

"You're fine," he said, moving his hands farther up her legs. "Just relax."

She let out a sigh, breaking eye contact. "I'm over thinking this. It's just sex. People do it all the time."

"Hey. You. Look at me." She turned her head back, locking eyes with him. "This is the easy part with us. This is what we're good at. You're good at this."

"I'm good at parts of this. Whether or not I'm good at sex…"

He cut her off. "You'll be fine." He started to pull at the elastic on her underwear, remembering how much she enjoyed a certain activity last time. Suddenly, she placed her hands over his, stopping him. "There are only three articles of clothing between me and you," she said, stating the obvious.

"I'm aware."

"I'm sorry. I'm acting like a complete idiot."

He smiled. "Stop apologizing."

"I didn't think I'd act this way. I mean I was good that day in your bedroom, wasn't I?'

"I enjoyed you up to a certain point."

"And now? I'm acting like I'm Amish or something."

"You're nervous. It's cute."

"Really?"

"Yeah," he pulled at her underwear again. "Trust me?"

"No."

"Fair enough." He slid toward her, resting his weight on his elbows. He stayed like that, barely touching her, enjoying the feel of her squirming beneath him. "Problem, Gilmore?"

"What are you doing?"

"Taking a break."

"Excuse me?" she huffed.

"I'm tired of doing all the work."

"Is that a challenge?'

"I have no idea what you're referring to. I'm just…" before he could finish his thought, she arched her body into his, catching his lips between hers.

She pushed against him, harder. He took this as his cue and pushed her underwear off her hips.

"Two," he mumbled into her mouth.

Her hands found his zipper and after a few tugs, his jeans were on the floor.

"One," she muttered, reaching inside his boxers, placing a hand around him.

His breath caught. He wasn't expecting that.

"Rory," he groaned. He moved a hand down, stopping her motions.

She froze.

"Another time," he struggled and she understood.

He was wound too tight for _that_.

She arched her body into him, nothing left between them.

* * *

"You want to cuddle?"

"No," Rory answered, quickly. "But I do appreciate the offer. It's just…cuddling is…"

"I get it. We're not the cuddling type." He reached down, finding his pants, and pulled out his pack of cigarettes. "Want one?"

She shrugged and pulled one out of the pack, sticking it in her mouth.

He leaned into her, lighting her cigarette. "I know you admire Audrey Hepburn and you'll probably name your spawn after her, but I think you're embodying Katherine much more right now."

She exhaled the smoke. "Really?"

"Freshly fucked. Smoking. Sexy as hell. Definitely Katherine."

"Thank you."

They smoked in silence for a few minutes, the only noise coming from Rory's computer. Beck was singing about some girl named Debra.

Rory eventually broke the silence. "So, what now?"

"Can't you just enjoy the quiet?" He lit another cigarette.

"I leave in two days."

"I'm well aware."

"This was…you were…"

"Awesome. I know."

"That's not what I was going to say."

"Mind blowing is another one I hear quite often."

"Please don't remind me of how often you do this."

He turned toward her, stubbing out his cigarette. "You know this is different."

"But as soon as I go to Harvard, you'll resume your daily orgies."

"I'll try to cut back, I promise."

"This is why we can't be boyfriend and girlfriend."

"I don't want to be your boyfriend."

"What?"

"I'm pretty sure you still hate me."

"I…"

"I'm a huge proponent of hate sex, so don't be ashamed."

"So that's what this was for you?'

"No."

"Well then, what was this?"

"Two friends expressing their appreciation for each other."

"It was more than that."

"You're the one that said this had to stay between us. And I agreed to that condition, so as far as I'm concerned, this never happened."

"So you fucked me and now you're going to forget about me?"

"There is no way I'll forget the feel of you."

She started to blush. "It was different than I expected."

"Good different?"

"Yeah," she smiled.

"I also won't forget how you look right now. Sex looks good on you."

"You always find a way to ruin things."

"It's a genuine compliment. Sex doesn't look good on some girls. But you wear it well."

He pulled all of her on top of him. "Don't go to Harvard."

She scrunched up her face. "What?"

"We have trust funds. Fuck higher education."

"You can't be serious."

"Try to lie to me and tell me you've ever been happier than you are right now."

"I got a pony for my fifth birthday. I was pretty happy then."

"So Rory Gilmore is happiest when she's riding things? I'll remember that."

He pulled her down, crashing his lips into hers.

He could feel her moving herself onto _him_. She let out a soft moan as soon as he was inside her.

He would never forget this.

* * *

Seven times. She had sex with Jess Mariano seven times.

"He was just so perfect and good at what he was doing. The first time was weird and tense and he was almost being too careful and I was tipsy and there were just a lot of hands and fumbling and then it was over. But after that, god, he was so good. I know it's because he's had practice and sex is like riding a bike but I'm pretty sure he is abnormally good at sex. There are things he does with his mouth…" she stopped, realizing what she was saying. "I sound like some sex crazed idiot right now, don't I?"

Greta was barely able to contain her excitement. "You're glowing, Miss Rory."

She pushed some hair behind her ears, nervous. "I'm shaky. Like all the time. I can't stop shaking. Is that normal? And I can't stop smiling. My face hurts. I want to stop smiling but I can't. See, right now, I'm consciously trying to stop smiling and I can't."

"So, what does this mean for you and Mr. Jess?"

Rory's smile faded a bit. "I leave tomorrow."

"It's not that far away."

"We can't do the relationship thing. We're not relationship people."

"So what's going to happen?"

"I'm going to go to Harvard tomorrow."

"That's it?"

"Long distance never works."

"I think you should try."

"I think you should worry about your lack of a sex life and forget about my soon to be non-existent one."

"I know you're only lashing out because you know I'm right."

"Stop it, Greta! We're not going to talk on the phone everyday or meet halfway to have picnics or hold hands or any of the other things that couples do. We're terrible people."

"But Mr. Jess knows all this and still loves you. Doesn't that mean something?"

"I'm glad we had sex. Isn't that enough?"

"I don't know, Miss Rory. Is it?"

* * *

There she was, standing outside his window, throwing rocks to get his attention.

He opened the window. "Why are you channeling Romeo? We don't have warring families. You can use the front door."

She shrugged. "This is my attempt at a grand, romantic gesture."

"Aren't you supposed to have a boom box?'

"I was on my way to the airport."

"And you decided to take a break and throw rocks at my window?"

"You didn't say goodbye!"

"You know I'm not a fan of goodbyes."

"You took my virginity! I get a goodbye!'

"Okay. Goodbye, Rory Gilmore."

"No."

"Didn't you just say you wanted a goodbye?"

"Don't treat me how you treat all the others."

"I assumed yesterday was a more than sufficient goodbye."

"Yesterday was…nice."

"Nice? We have sex seven times and you define that as nice?"

"Can I come up? I'd rather all of Hartford didn't hear about our sex life."

"I'm not letting down my hair."

She scoffed. "I'll use the front door."

He rolled his eyes. "How modern of you."

* * *

Rory walked into his room.

Jess arched an eyebrow. "Why are you fidgeting? Are you nervous? Or more specifically, is your vagina nervous?"

She held up her hand. "Don't say things like that."

"Okay."

"I'm supposed to be emotionally terrorizing my roommate right now."

"Why aren't you?"

"Because you got in my head."

"And other places."

"Again with that shit?"

"Sorry. I'll stop."

"Thank you."

He smirked. "So I'm in your head, huh?"

"Unfortunately."

"What am I saying?"

"Things that make me not want to go to Harvard."

He crossed his arms over his chest, becoming defensive. "So why are you here? Do you need me to set you free again?"

"No."

"Then why?"

And she started. "I'm a terrible person. Like there's Hitler, my grandmother, a few dudes who raped and pillaged villages, Nicolas Sparks. And then me. Most people don't know exactly how awful I am. But you do and for some reason, you still love me."

He shrugged. "I'm in love with the worst person."

"And then there's you. You fuck anything that moves. You made my virginity a game. And I'm sure you've sent hundreds of girls to convents. We're terrible people. I'd be a terrible girlfriend."

"I'd be a terrible boyfriend," he reassured her.

"Then let's be a terrible together."

"Aren't you worried we'll end up like Liz and Dick?"

"Why are you all of a sudden playing the role of the negative one?"

"Your attitude was different before…"

She cut him off. "I'm not some lovesick idiot that falls in love with the guy that took her virginity! Don't insult me by comparing me to those kind of girls," she said, rolling her eyes.

"You need to forget about me."

"What?"

"I'm not good for you."

"You constantly told me to stop doing what everyone else wanted me to do, to stop living under some false delusion of what my life is supposed to be. And finally, when I'm ready, you decide to push me away?"

"I don't want to hurt you."

"Then don't."

"It's not that simple."

"I love you. Not the idea of you. Not what I want you to be. You."

She could finally breathe.

"I know."

"Don't Han Solo this moment."

"You know how I feel."

"I'd really like to hear it again, you know, for reassurance purposes."

"They're just words."

"Is this your subtle way of telling me you don't love me or something?"

"No."

"Then why won't you say it."

"Because I know it bothers you."

She smiled. "I don't know why I love you sometimes. Most of the time, actually."

"I've heard I'm irresistible."

"You're okay."

"You're not so bad yourself."

She rocked back on her heels. "So is this how we're going to end?"

"What's so wrong with leaving things unsettled?"

"I need something to…"

"I'll call you," he offered.

She bit down on her lip. "I shouldn't have stopped by. I'm sorry for wasting your time."

She turned to leave but he grabbed her wrist. "I'm glad you came by." He leaned down, placing a kiss in her hair. "Don't fall in love with some dick at Harvard."

"Don't fuck…well, everything."

"I won't."

She paused, unsure of what her next move should be. "Come here." She rose up on her tiptoes, capturing Jess' lips in hers.

She pulled away. "I have a break in seven weeks."

"I know."

She smiled. "As a terrible boyfriend, I'm pretty sure you aren't supposed to know things like that."

He shrugged. "I hate being predictable."

She just stood there. "My feet won't move," she said, dumbly.

"If you stay much longer, I'll be forced to remove your clothing, which will make you unfashionably late to orientation."

"I'm going."

She turned to leave but he stopped her, again. "Hey, Gilmore."

She sighed. "Jess, I have to go..."

He quickly cut in. "Don't change your mind."

She bit her lip. "About what?"

"Me."

She smiled. "I don't like anyone else."

THE END

* * *

**Ending Author's Note**: I know. I can't believe I gave you a semi-happy ending either. I guess I was tried of being miserable. You can only take so much misery and I overloaded you guys with it. You might think this was a bitch out, that I was too much of a conformer to have a truly miserable ending, but I don't know. The entire story was about two people that could never get their shit together and be together. And if I did that again in chapter 9, well, I might as well have stopped at 8, cause that was a sufficient ending.

But if you hate me and are planning my murder, no axes, please. And pop some champagne first.

But no matter what, thank you, people of the internets.

**Reviewers**: What's there left to say? You're wonderful. I adore you. I hope you still adore me. Let me know what you think. Seriously. Write me a novel, full of conflicted statements and irony. I love irony.

(By the wayside, I almost titled the chapter "We have trust funds. Fuck higher education." I'm really proud of that creation).

Goodbye, for now. Or as Jigga Man would say, on to the next one, whatever that one may be.

Ideas are welcome. Drugs are encouraged.


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